6,7,8,9-tetrahydro-5H-benzo(7)annulen-5-amine → (1H-Benzoimidazol-2-yl)-(6,7,8,9-tetrahydro-5H-benzocyclohepten-5-yl)amine

HRID 16555Notes

Reaction equation

HRID 16555 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.[CH:11]1[C:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([NH2:22])[C:15]=2[CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[NH:3][C:2]=1[NH:22][CH:21]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:16]=2[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 252446,7,8,9-tetrahydro-5H-benzo(7)annulen-5-amineHCID 785722-Chlorobenzimidazole

Product 1

HCID 11507384(1H-Benzoimidazol-2-yl)-(6,7,8,9-tetrahydro-5H-benzocyclohepten-5-yl)amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared from 2-chlorobenzimidazole and racemic 6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ylamine (prepared by Procedure B from 1-benzosuberone) by Procedure A (reflux in toluene for 2 days). The product was isolated from the reaction mixture by preparative LCMS to give the title compound as the free base and as a mixture of enantiomers (white solid, mp 203-205° C.). MS(ES+) m/z 278 ([M+1]+, 100). 1NMR (DMSO-d6) δ 1.28-1.39 (m, 1H), 1.65-2.02 (m, 5H), 2.83-2.97 (m, 2H), 5.03 (t, 1H), 6.77-6.89 (m, 2H), 7.05-7.29 (m, 7H), 10.6 (s, 1H).

Workup

  1. customThe product was isolated from the reaction mixture by preparative LCMS

Sources & evidence

ORD record
ord-1da6b93181ed4f949878c863288cd8be
Source dataset
uspto-grants-2010_06
Patent number
US07737167B2

Reaction notes

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