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

HRID 18726Notes

Reaction equation

HRID 18726 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, 3 H), 7.60-7.30 (m, 5 H), 7.20-7.00 (m, 6 H), 7.00-6.85 (m, 4 H), 5.49 (s, 2 H), 4.59 (d, 2 H); 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-728e2f40af9e48e5968780915d01c0d5
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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