4-Fluorobenzoyl chloride → N-{[1-(Dimethylamino)cyclohexyl]methyl}-4-fluorobenzamide hydrochloride (1:1)

HRID 2071982Notes

Reaction equation

HRID 2071982 reaction equation
[NH2:1][CH2:2][C:3]1([N:9]([CH3:11])[CH3:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[F:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([Cl:19])=[O:18])=[CH:15][CH:14]=1>N1C=CC=CC=1>[ClH:19].[F:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:1][CH2:2][C:3]2([N:9]([CH3:11])[CH3:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)=[O:18])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 21134031-(Aminomethyl)-N,N-dimethylcyclohexan-1-amine

Product 1

HCID 21409921N-{[1-(Dimethylamino)cyclohexyl]methyl}-4-fluorobenzamide hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-aminomethylcyclohexyldimethylamine (1.0 g), 4-fluorobenzoyl chloride (2 ml) and pyridine (10 ml) was allowed to stand at room temperature for 1 hr. The crystalline material produced was filtered and recrystallised several times from ethanol/ether to give colourless needles of 1-(4-fluorobenzamidomethyl)-cyclohexyl dimethylamine hydrochloride m.p. 238°-239°.

Workup

  1. customThe crystalline material produced
  2. filtrationwas filtered
  3. customrecrystallised several times from ethanol/ether

Sources & evidence

ORD record
ord-1cb8c58074ca46c58d84407e9d65543e
Source dataset
uspto-grants-1977_09
Patent number
US04049663

Reaction notes

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