Dicyclohexylcarbodiimide → 1-[3-[[3-(Piperidin-1-yl)propylamino]carbonyl]propyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole dihydrochloride salt

HRID 1383977Notes

Reaction equation

HRID 1383977 reaction equation
[C:1]([CH2:4][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].[N:26]1([CH2:32][CH2:33][CH2:34][NH2:35])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[ClH:25].[ClH:25].[N:26]1([CH2:32][CH2:33][CH2:34][NH:35][C:1]([CH2:4][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])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 19049Piperidine-1-propylamineHCID 757711-HydroxybenzotriazoleHCID 211885191-(3-Carboxypropyl)-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Product 1

HCID 211885251-[3-[[3-(Piperidin-1-yl)propylamino]carbonyl]propyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole dihydrochloride saltYield 263%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 1-[3-carboxypropyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (0.540 g, 1.5 mmol) in N,N-dimethylformamide (60 ml) were added sequentially 3-(piperidin-1-yl)propylamine (235 mg, 1.1 eq), 1-hydroxybenzotriazole (223 mg, 1.1 eq), and dicyclohexylcarbodiimide (340 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 0.731 grams of the title compound as an orange solid.

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-9c2f1ab3f19440d68010605b2badeeba
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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