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

HRID 261055Notes

Reaction equation

HRID 261055 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]1([CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[CH3:30][O:31][C:32]1[CH:40]=[C:39]([NH:41][C:42](=[O:44])[CH3:43])[C:38]([Cl:45])=[CH:37][C:33]=1[C:34](O)=[O:35]>C(Cl)Cl>[OH2:31].[ClH:45].[CH:16]1([CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:34](=[O:35])[C:33]3[CH:37]=[C:38]([Cl:45])[C:39]([NH:41][C:42](=[O:44])[CH3:43])=[CH:40][C:32]=3[O:31][CH3:30])[CH2:25][CH2:24]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 64969411-(Cyclohexylmethyl)piperidin-4-amineHCID 109884964-Acetamido-5-chloro-2-methoxybenzoic acid

Product 1

HCID 20395819N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide hydrochloride monohydrateYield 119.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N'-dicyclohexylcarbodiimide (10.3 g; 0.05 moles) and 1-cyclohexylmethyl-4-aminopiperidine (9.8 g; 0.05 moles) were added successively to a solution of 2-methoxy-4-acetamido-5-chlorobenzoic acid (12.1 g; 0.05 moles) in methylene chloride (250 ml). After stirring overnight at room temperature, the insoluble N,N'-dicyclohexylurea was filtered off, the solution was washed with water, dried (Na2SO4) and the solvent removed in vacuo. The residue was recrystallized and the product converted into its hydrochloride to give 14.2 g of N-(1-cyclohexylmethylpiperid-4-yl)-2-methoxy-4-acetamido-5-chlorobenzamide hydrochloride monohydrate, m.p. 219°-221° C.

Workup

  1. filtrationthe insoluble N,N'-dicyclohexylurea was filtered off
  2. washthe solution was washed with water
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was recrystallized

Sources & evidence

ORD record
ord-9e62b10c89f644c49f4826dcc4b17295
Source dataset
uspto-grants-1979_08
Patent number
US04163789

Reaction notes

Loading…