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Benzylamine → (RS) 1-[3-[[benzylaminoamino]carbonyl]butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

HRID 1383978
Notes
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Reaction equation

HRID 1383978 reaction equation
[C:1]([CH:4]([CH3:26])[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].[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O[N:36]1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:27]([NH:34][NH:36][C:1]([CH:4]([CH3:26])[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:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)=[O:2])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 211885121-(3-Carboxybutyl)-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Product 1

HCID 21188759(RS) 1-[3-[[benzylaminoamino]carbonyl]butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazoleYield 106.9%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of (RS) 1-[3-carboxybutyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (0.500 g, 1.4 mmol) in N,N-dimethylformamide (40 ml) were added sequentially benzylamine (165 mg, 1.1 eq), 1-hydroxybenzotriazole (208 mg, 1.1 eq), and dicyclohexylcarbodiimide (317 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 0.714 grams of the title product as a white 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-8302c6855237451085a1e4d1fbaf161c
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06255494B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes