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

HRID 1383972Notes

Reaction equation

HRID 1383972 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)(O)=[O:2].[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[N:33]1([C:1]([CH:4]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=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:2])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 211886901-(4-Phenyl-3-carboxybutyl)-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Product 1

HCID 211886331-[3-[(Piperidin-1-yl)carbonyl]-4-phenylbutyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazoleYield 162.1%

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 piperidine (206 mg, 1.1 eq), 1-hydroxy-benzotriazole (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 concntrated 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 1.84 grams of a tan foam.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washwashed once with water (200 ml)
  3. dry with materialdried over potassium carbonate
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-b1049fca767d417b954803a765c721e8
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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