Hydrochloric Acid → (4S,5R)-N-benzyl-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-amine;hydrochloride

HRID 2053519Notes

Reaction equation

HRID 2053519 reaction equation
[ClH:1].C(OC([N:9]1[C@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:11]=[C:10]1[NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=O)(C)(C)C>CCOC(C)=O>[ClH:1].[C:14]1([C@H:13]2[C@@H:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:11][C:10]([NH:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[N:9]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68567154tert-butyl (4S,5R)-2-(benzylamino)-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

Product 1

HCID 68570665(4S,5R)-N-benzyl-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-amine;hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen chloride is bubbled into a solution of 77 (200 mg, 0.47 mmol) in EtOAc (10 mL) for 1 min, and the solution is stirred at RT overnight. The solvent is removed by rotary evaporation, and the residue is crystallized from dichloromethane and Et2O to give 130 mg of the product 78. 1H NMR (DMSO-d6) δ 9.80-8.30 (m, 3H), 7.60-7.30 (m, 5H), 7.20-7.00 (m, 6H), 7.00-6.85 (m, 4H), 5.49 (s, 2H), 4.59 (d, 2H); MS: m/z 328 (M++1).

Workup

  1. customThe solvent is removed by rotary evaporation
  2. customthe residue is crystallized from dichloromethane and Et2O

Sources & evidence

ORD record
ord-149f2287fcb84cf9b32d5bb2b6110a93
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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