Dicyclohexylcarbodiimide → HCID 12821274, compound

HRID 1494534Notes

Reaction equation

HRID 1494534 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:30][O:31][C:32]1[CH:40]=[C:39]([NH:41][C:42](=[O:44])[CH3:43])[C:38]([N+:45]([O-:47])=[O:46])=[CH:37][C:33]=1[C:34](O)=[O:35].[C:48]([OH:55])(=[O:54])/[CH:49]=[CH:50]/[C:51]([OH:53])=[O:52]>C(Cl)Cl.CO>[C:48]([OH:55])(=[O:54])/[CH:49]=[CH:50]/[C:51]([OH:53])=[O:52].[CH2:16]([N:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:34](=[O:35])[C:33]2[CH:37]=[C:38]([N+:45]([O-:47])=[O:46])[C:39]([NH:41][C:42](=[O:44])[CH3:43])=[CH:40][C:32]=2[O:31][CH3:30])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 4158521-Benzyl-4-piperidylamineHCID 444972Fumaric AcidHCID 198285344-(Acetylamino)-2-methoxy-5-nitrobenzoic acid

Product 1

HCID 12821274HCID 12821274, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N,N'-Dicyclohexylcarbodiimide (4.12 g; 0.02 moles) and 1-benzyl-4-aminopiperidine (3.8 g; 0.02 moles) were added successively to a solution of 2-methoxy-4-acetamido-5-nitrobenzoic acid (5.1 g; 0.02 moles) in methylene chloride (125 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 to give a solid. It was suspended in hot methanol and treated with the stoichiometric amount of fumaric acid to give a solution from which the N-(1-benzylpiperid-4-yl)-2-methoxy-4-acetamido-5-nitrobenzamide fumarate (6.2 g) crystallized. After recrystallization from methanol this compound melted at 204°-206° 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. customto give a solid

Sources & evidence

ORD record
ord-1d0b1f6b1cc94599a70d7c95695caff8
Source dataset
uspto-grants-1991_06
Patent number
US05026858

Reaction notes

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