Methyl iodide → Tert-butyl 4-(4-chlorophenyl)-4-methoxymethylpiperidine-1-carboxylate

HRID 405945Notes

Reaction equation

HRID 405945 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:21][OH:22])[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+].[CH3:25]I>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:21][O:22][CH3:25])[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58117682Tert-butyl 4-(4-chlorophenyl)-4-hydroxymethylpiperidine-1-carboxylate

Product 1

HCID 58117854Tert-butyl 4-(4-chlorophenyl)-4-methoxymethylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

440 mg tert-butyl 4-(4-chlorophenyl)-4-hydroxymethylpiperidine-1-carboxylate are placed in 2.5 ml dimethylformamide and 92 mg sodium hydride (60% in mineral oil) are added. The reaction mixture is stirred for 30 min at ambient temperature, then 95 μl methyl iodide are added. After 1 h the reaction mixture is poured onto ice and the product is extracted with diethyl ether. 370 mg product are obtained as an oil.

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-64b68dc6f9c64a319bce51fd0e70b11d
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Reaction notes

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