Dicyclohexylcarbodiimide → 1-[3-[3-(Piperidin-1-yl)propylcarbamoyl]-4-phenylbutyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

HRID 1383975Notes

Reaction equation

HRID 1383975 reaction equation
[C:1]([CH:4]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=2[N:9]=[C:8]1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)([OH:3])=O.[NH2:33][CH2:34][CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[N:37]1([CH2:36][CH2:35][CH2:34][NH:33][C:1]([CH:4]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:5][CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=3[N:9]=[C:8]2[CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[O:3])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 19049Piperidine-1-propylamineHCID 757711-HydroxybenzotriazoleHCID 211886901-(4-Phenyl-3-carboxybutyl)-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Product 1

HCID 211888191-[3-[3-(Piperidin-1-yl)propylcarbamoyl]-4-phenylbutyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazoleYield 107.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 1-[3-carboxy-4-phenylbutyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (1.0 g, 2.2 mmol) in N,N-dimethylformamide (75 ml) were added sequentially 1-amino-3-(piperidin-1-yl)propane (345 mg, 1.1 eq), 1-hydroxybenzotriazole (327 mg, 1.1 eq), and dicyclohexylcarbodiimide (500 mg, 1.1 eq). The resulting mixture was then stirred under a nitrogen atmosphere at room temperature for 64 hours. The reaction mixture was then filtered and the resulting filtrate was concentrated under reduced pressure. This residue was taken into ethyl acetate (200 ml) and washed once with water (200 ml), dried over potassium carbonate. The solvents were removed in vacuo to yield 1.35 grams of an orange foam.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe resulting filtrate was concentrated under reduced pressure
  3. washwashed once with water (200 ml)
  4. dry with materialdried over potassium carbonate
  5. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-260d1141f77148deb90e73ae210a1adf
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

Loading…