1,2,3,4-Tetrahydroisoquinoline → 1-[3-[(1,2,3,4-Tetrahydroisoquinolin-1-yl)carbonyl]butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

HRID 1383976Notes

Reaction equation

HRID 1383976 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]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][NH:28]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH:27]1([C:1]([CH:4]([CH3:26])[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:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[O:2])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][NH:28]1

Participants

6

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 211885121-(3-Carboxybutyl)-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Product 1

HCID 211888161-[3-[(1,2,3,4-Tetrahydroisoquinolin-1-yl)carbonyl]butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazoleYield 115.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 1-[3-carboxybutyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (0.800 g, 2.2 mmol) in N,N-dimethylformamide (50 ml) were added sequentially 1,2,3,4-tetrahydroisoquinoline (322 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 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 1.24 grams of a dark oil.

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-ebb78c1ebe5b471295ee0617557efa29
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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