Methylamine → 4,4-difluoro-N-methylcyclohexan-1-amine

HRID 2086560Notes

Reaction equation

HRID 2086560 reaction equation
[F:1][C:2]1([F:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[CH3:10][NH2:11].[H][H]>CO.[Pd].[OH-]>[F:1][C:2]1([F:9])[CH2:7][CH2:6][CH:5]([NH:11][CH3:10])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 157890924,4-DifluorocyclohexanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 222249964,4-difluoro-N-methylcyclohexan-1-amineYield 50%

Reagents, catalysts & solvents 2

HCID 14345455HCID 14345455, compoundCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared from 4,4-difluoro-cyclohexanone (prepared from 8,8-Difluoro-1,4-dioxa-spiro[4.5]decane by deprotection with sulfuric acid under standard conditions) and methylamine by reductive amination under standard conditions (Pd hydroxide in methanol, 1 atm hydrogen) in ˜50% yield. Recrystallization of the hydrochloride from ethanol/diethylether afforded analytical pure material. Light-brown solid, mp 137-144° C. MS: m/e=186 (M+H+).

Workup

  1. customRecrystallization of the hydrochloride from ethanol/diethylether afforded analytical pure material

Sources & evidence

ORD record
ord-212987368202447389de236b69cef947
Source dataset
uspto-grants-2004_04
Patent number
US06727247B2

Reaction notes

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