2-Chlorobenzimidazole → (1H-Benzoimidazol-2-yl)-(5,7-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)amine

HRID 16558Notes

Reaction equation

HRID 16558 reaction equation
Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][C:12]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]2[C:13]=1[CH2:14][CH2:15][CH2:16][CH:17]2[NH2:23]>>[N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[NH:3][C:2]=1[NH:23][CH:17]1[C:18]2[C:13](=[C:12]([CH3:11])[CH:21]=[C:20]([CH3:22])[CH:19]=2)[CH2:14][CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 785722-ChlorobenzimidazoleHCID 111267915,7-Dimethyl-1,2,3,4-tetrahydronaphthalen-1-amine

Product 1

HCID 11623447(1H-Benzoimidazol-2-yl)-(5,7-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)amine

Procedure

The title compound was prepared from 2-chlorobenzimidazole and 5 ,7-dimethyl-1,2,3,4-tetrahydro-1-naphthylamine (prepared by Procedure B from 5,7-dimethyl-1-tetralone) by Procedure A (60 min at 170° C. followed by 20 min at 200° C.). The product was purified by recrystallisation to give the title compound as the free base and as a mixture of enantiomers (white solid, mp 250-252° C.). MS(ES+) m/z 292 ([M+1]+, 100).

Workup

  1. customThe product was purified by recrystallisation

Sources & evidence

ORD record
ord-2b886003c897496299a5a3d19c74f014
Source dataset
uspto-grants-2010_06
Patent number
US07737167B2

Reaction notes

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