1-(Cyclohexylmethyl)piperidin-4-amine → N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide hydrochloride monohydrate

HRID 261051Notes

Reaction equation

HRID 261051 reaction equation
[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:15][O:16][C:17]1[CH:25]=[C:24]([NH:26][C:27](=[O:29])[CH3:28])[C:23]([Cl:30])=[CH:22][C:18]=1[C:19]([Cl:21])=[O:20]>C(C(C)=O)C>[OH2:16].[ClH:21].[CH:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:19](=[O:20])[C:18]3[CH:22]=[C:23]([Cl:30])[C:24]([NH:26][C:27](=[O:29])[CH3:28])=[CH:25][C:17]=3[O:16][CH3:15])[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 64969411-(Cyclohexylmethyl)piperidin-4-amineHCID 113799924-Acetamido-5-chloro-2-methoxybenzoyl chloride

Product 1

HCID 20395819N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide hydrochloride monohydrateYield 160.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

To a solution of 1-cyclohexylmethyl-4-aminopiperidine (9.8 g; 0.05 moles) in methyl ethyl ketone (100 ml), a solution of 2-methoxy-4-acetamido-5chlorobenzoyl chloride (14.4 g, 0.055 moles) in methyl ethyl ketone (100 ml) was slowly added at a temperature between 0° and 5° C. The mixture was stirred at the same temperature for 1 hour followed by 4 hours at room temperature. The precipitated solid was filtered off, washed with methyl ethyl ketone and recrystallized from a mixture of ethanol-water to give N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide hydrochloride monohydrate (21 g), m.p. 219°-221° C.

Workup

  1. waitfollowed by 4 hours at room temperature
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with methyl ethyl ketone
  4. customrecrystallized from a mixture of ethanol-water

Sources & evidence

ORD record
ord-4b5f29fab5e7401b9e026568936feb0d
Source dataset
uspto-grants-1979_08
Patent number
US04163789

Reaction notes

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