N-Boc-(2,3-dimethoxyphenyl)-4-piperidinylmethanone

Base Information

• Chemical Name: N-Boc-(2,3-dimethoxyphenyl)-4-piperidinylmethanone
• CAS No.: 139290-71-4
• Molecular Formula: C19H27NO5
• Molecular Weight: 349.427
• Mol file: 139290-71-4.mol

Synonyms:

Chemical Property of N-Boc-(2,3-dimethoxyphenyl)-4-piperidinylmethanone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 450.718oC at 760 mmHg
• Flash Point: 226.386oC
• PSA: 65.07000
• Density: 1.128g/cm3
• LogP: 3.47150
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

95% ^*data from raw suppliers

N-Boc-(2,3-dimethoxyphenyl)-4-piperidinylmethanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate in the preparation of serotonin 5-HT2a receptor antagonists

Technology Process of N-Boc-(2,3-dimethoxyphenyl)-4-piperidinylmethanone

There total 16 articles about N-Boc-(2,3-dimethoxyphenyl)-4-piperidinylmethanone 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: 90.0%

4-(2,3-dimethoxybenzoyl)piperidine hydrochloride (243640-36-0) + di-tert-butyl dicarbonate (24424-99-5) → 4-(2,3-Dimethoxybenzoyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (139290-71-4)

Guidance literature:

With sodium hydroxide; In ethanol; water; toluene;

Reference yield: 90.0%

3-lithio-1,2-dimethoxybenzene (2785-95-7) + tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (139290-70-3) → 4-(2,3-Dimethoxybenzoyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (139290-71-4)

Guidance literature:

In tetrahydrofuran; hexane; at -17 - 25 ℃; for 18.5h; Product distribution / selectivity;

Reference yield: 75.0%

1,2-dimethoxybenzene (91-16-7) + tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (139290-70-3) → 4-(2,3-Dimethoxybenzoyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (139290-71-4)

Guidance literature:

1,2-dimethoxybenzene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 2.75h; Inert atmosphere; Schlenk technique;

tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate; In tetrahydrofuran; hexane; at -20 - 20 ℃; for 21h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c3cc45545a

upstream raw materials:

1,2-dimethoxybenzene

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

2,2'-oxybis(2-methyl-propane)

Downstream raw materials:

R-(+)-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol

(-)-MDL 100907

(+/-)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol

(2,3‐dimethoxyphenyl)(piperidine‐4‐yl)methanol

Refernces

• 1、 Fuentes, Jose A.,Carpenter, Ian,Kann, Nina,Clarke, Matthew L.. "Highly enantioselective hydrogenation and transfer hydrogenation of cycloalkyl and heterocyclic ketones catalysed by an iridium complex of a tridentate phosphine-diamine ligand". supporting information. p. 10245 - 10247. Retrieved 2013/10/22.
• 2、 -. "COMBINATION OF A HYPNOTIC AGENT AND R (+)-ALPHA-(2,3-DIMETHOXY-PHENYL)-1-[2-(4-FLUOROPHENYL)ETHYL]-4-PIPERIDINEMETHANOL AND THERAPEUTIC APPLICATION THEREOF". Page/Page column 10-11. . Retrieved 2008/12/06.