[6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ium-1-ylethoxy)phenyl]methanone;chloride

Base Information

• Chemical Name: [6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ium-1-ylethoxy)phenyl]methanone;chloride
• CAS No.: 82640-04-8
• Molecular Formula: C28H28ClNO4S
• Molecular Weight: 510.054
• Hs Code.: 2934990002
• Pharos Ligand ID: Z21APBSNPM3W
• Mol file: 82640-04-8.mol

Synonyms:[6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ium-1-ylethoxy)phenyl]methanone;chloride;MLS001304731;HMS2233M16;HMS3372E10;AKOS015960340;SMR000752510;Evista;[6-Hydroxy-2-(4-hydroxyphenyl)-benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone Hydrochloride;Keoxifene

Chemical Property of [6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ium-1-ylethoxy)phenyl]methanone;chloride

Chemical Property:

• Appearance/Colour: Light yellow solid
• Vapor Pressure: 1.56E-19mmHg at 25°C
• Melting Point: 143-147oC
• Refractive Index: 1.654
• Boiling Point: 728.2 °C at 760 mmHg
• Flash Point: 394.2 °C
• PSA: 98.24000
• Density: 1.285g/cm3
• LogP: 6.81510
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: 28 mg/mL, soluble
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 509.1427572
• Heavy Atom Count: 35
• Complexity: 655

Purity/Quality:

99% ^*data from raw suppliers

Raloxifene hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC[NH+](CC1)CCOC2=CC=C(C=C2)C(=O)C3=C(SC4=C3C=CC(=C4)O)C5=CC=C(C=C5)O.[Cl-]
• Description: Raloxifene was launched as Evista in the US for the prevention of postmenopausal osteoporosis. It is noteworthy that this molecule was formerly under development as keoxifene for breast cancer and prostatic hypertrophy. Raloxifene can be prepared by acylation of 6-methoxy-2-(4-methoxyphenyl) benzothiophene followed by simultaneous demethylation of both methoxy groups. Raloxifen is a selective estrogen receptor modulator, exerting antiestrogenic action on certain tissues (breast) and also estrogenic action on bone metabolism or serum lipids. In normal early postmenopausal women, 200 mg daily produced a trend towards suppression of estrogen effects. Raloxifen impeded bone loss in osteoporosis. A two-year study in postmenopausal women with an increased risk for osteoporosis showed that Raloxifen markedly prevented non-traumatic vertebral fractures. Results of several clinical studies demonstrated that Raloxifen appreciably reduced the risk of developing breast cancer. Moreover, it had favourable effect on lipid profiles without having the potential side-effects of estrogen-based therapies. Several extensions for different uses of this molecule are planned, for example growth disorder, obesity, colon tumor and skin atrophy. No serious drug-related events have been reported in the limited number of clinical trials.
• Uses: Raloxifene hydrochloride can be used as a nonsteroidal, selective estrogen receptor modulator (SERM). Antiosteoporotic. amino acid, nutrient. A nonsteroidal, selective estrogen receptor modulator (SERM). Antiosteoporotic.Insoluble in water. Labeled Raloxifene, intended for use as an internal standard for the quantification of Raloxifene by GC- or LC-mass spectrometry.
• Clinical Use: Treatment and prevention of osteoporosis in post menopausal women
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: antagonism of anticoagulant effect of coumarins. Colestyramine: reduced absorption of raloxifene - avoid.

Technology Process of [6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ium-1-ylethoxy)phenyl]methanone;chloride

There total 29 articles about [6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ium-1-ylethoxy)phenyl]methanone;chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

[2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride (84541-36-6) → raloxifene hydrochloride (82640-04-8)

Guidance literature:

[2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride; With boron trichloride; In dichloromethane; at 2 - 20 ℃; for 52.25h;

With methanol; In dichloromethane; at 12 ℃; for 1.08333h; Product distribution / selectivity; Reflux;

Reference yield: 92.0%

[6-Methoxy-2-(4-Methoxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1-Piperidinyl)ethoxy]phenyl] Methanone (84541-38-8) → raloxifene hydrochloride (82640-04-8)

Guidance literature:

With N,N-diethylaniline; ethanethiol; In dichloromethane; at 32 - 34 ℃; for 2h; Solvent;

Reference yield: 70.4%

6-acetoxy-2-(4-acetoxyphenyl)benzo[b]thiophene (84449-63-8) + 4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride (84449-80-9) → raloxifene hydrochloride (82640-04-8)

Guidance literature:

4-(2-piperidin-1-ylethoxy)benzoic acid hydrochloride; With pyridine; thionyl chloride; In dichloromethane; for 1h; Heating / reflux;

6-acetoxy-2-(4-acetoxyphenyl)benzo[b]thiophene; In dichloromethane;

With hydrogenchloride; sodium hydroxide; water; aluminum (III) chloride; more than 3 stages;

upstream raw materials:

[2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride

3-methoxybenzenethiol

2-(4'-methoxyphenyl)-6-methoxybenzothiophene

4-(2-(piperidin-1-yl)ethoxy)benzoyl chloride

Downstream raw materials:

[6-hydroxy-2-(4-hydroxyphenyl)-benzothiophen-3-yl]-[4-[2-(1-piperidyl)ethoxy]phenyl]-methanone hydrochloride monohydrate

[6-hydroxy-2-(4-hydroxyphenyl)-benzothiophene-3-yl]-[4-[2-(1-piperidyl)ethoxy]phenyl]methanone sulfamate

raloxifene N-oxide

(6-((tert-butyldimethylsilyl)oxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone

Refernces

• 1、 -. "Novel solvated crystalline of Raloxifene hydrochloride and process for preparing Raloxifene hydrochloride monohydrate". Paragraph 0045; 0047. . Retrieved 2016/10/09.
• 2、 -. "A process for preparing benzo[b]thiophene derivatives". Page/Page column 34. . Retrieved 2011/06/10.