Methyl iodide → 1-Tert-butoxycarbonyl-4-(4-chlorophenyl)-4-methoxypiperidine

HRID 1751811Notes

Reaction equation

HRID 1751811 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:21])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([O:21][CH3:24])[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21997555tert-Butyl 4-(4-chlorophenyl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 219975781-Tert-butoxycarbonyl-4-(4-chlorophenyl)-4-methoxypiperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

790 mg tert-butyl 4-(4-chlorophenyl)-4-hydroxypiperidine-1-carboxylate are placed in 5 ml dimethylformamide and 193 mg sodium hydride (60% in mineral oil) are added. The reaction mixture is stirred for 30 min at ambient temperature, then 267 μl methyl iodide are added. After 1 h the reaction mixture is poured onto ice and the product is extracted with diethyl ether. 650 mg product are obtained in the form of an oil. Analytical HPLC-MS (method B): RT==1.88 min.

Workup

  1. additionAfter 1 h the reaction mixture is poured onto ice
  2. extractionthe product is extracted with diethyl ether

Sources & evidence

ORD record
ord-cdc554d68b4d46b89904bc7470e0d1a7
Source dataset
uspto-grants-2015_10
Patent number
US09161927B2

Reaction notes

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