Dicyclohexylcarbodiimide → HCID 20513278, compound

HRID 1163893Notes

Reaction equation

HRID 1163893 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([N:23]1[CH2:28][CH2:27][CH:26]([NH:29][CH3:30])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:31][O:32][C:33]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:34]=1[C:35](O)=[O:36].[C:43]([OH:50])(=[O:49])/[CH:44]=[CH:45]/[C:46]([OH:48])=[O:47]>C(Cl)Cl>[C:43]([OH:50])(=[O:49])/[CH:44]=[CH:45]/[C:46]([OH:48])=[O:47].[CH3:30][N:29]([CH:26]1[CH2:27][CH2:28][N:23]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:24][CH2:25]1)[C:35](=[O:36])[C:34]1[CH:38]=[C:39]([Cl:42])[CH:40]=[CH:41][C:33]=1[O:32][CH3:31]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 769705-Chloro-o-anisic acidHCID 444972Fumaric AcidHCID 41361281-benzyl-N-methylpiperidin-4-amine

Product 1

HCID 20513278HCID 20513278, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N'-dicyclohexylcarbodiimide (10.3 g; 0.05 moles) and 1-benzyl-4-methylaminopiperidine (10.2 g; 0.05 moles) were added successively to a solution of 2-methoxy-5-chlorobenzoic acid (9.3 g; 0.05 mole) 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 to give an oil. It was salified with fumaric acid as described in Example 1 to give 10.3 g of N-methyl-N-(1-benzylpiperid-4-yl)-2-methoxy-5-chlorobenzamide fumarate, m.p. 192°-194° 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 an oil

Sources & evidence

ORD record
ord-3e262cff409f46bbaa946ad0b8574510
Source dataset
uspto-grants-1983_01
Patent number
US04367232

Reaction notes

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