Hydrochloric Acid → (4S,5R)-N-[(3-fluorophenyl)methyl]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-amine;hydrochloride

HRID 2053529

Reaction equation

HRID 2053529 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]=[C:30]([F:34])[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:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)=[N:9]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68569694tert-butyl (4S,5R)-2-[(3-fluorophenyl)methylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

Product 1

HCID 68569066(4S,5R)-N-[(3-fluorophenyl)methyl]-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 87 (1.5 g, 3.37 mmol) in EtOAc (30 mL) for 1 min, and the solution is stirred at RT overnight. The solvent is removed by rotary evaporation, and the residue crystallized from dichloromethane and Et2O to give 1.05 g of the product 88. 1H NMR (DMSO-d6) δ 9.28 (t, 1H), 8.68 (s, 1H), 8.15 (s, 1H), 7.35-7.10 (m, 3H), 7.10-6.80 (m, 7H), 6.80-6.50 (m, 4H), 5.03 (s, 1H), 4.80-4.45 (m, 2H); MS: m/z 346 (M++1).

Workup

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

Sources & evidence

ORD record
ord-3ce60218560b4bcc89211bc92abaa75d
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

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