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

HRID 18734Notes

Reaction equation

HRID 18734 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][C:31]([F:34])=[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][C:31]([F:34])=[CH:32][CH:33]=3)=[N:9]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68568680tert-butyl (4S,5R)-2-[(4-fluorophenyl)methylamino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

Product 1

HCID 68568666(4S,5R)-N-[(4-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 85 (0.69 g, 1.58 mmol) in EtOAc (40 mL) for 2 min, and the solution is stirred at RT overnight and then at 45° C. for 3 h. The solvent is removed by rotary evaporation, and the residue crystallized from dichloromethane and Et2O to give 0.52 g of the product 86. 1H NMR (DMSO-d6) δ 9.80-8.40 (m, 3 H), 7.60-7.45 (m, 2 H), 7.35-7.25 (m, 2 H), 7.15-6.95 (m, 6 H), 6.95-6.80 (m, 4 H), 5.50 (s, 2 H), 4.58 (d, 2 H); MS: m/z 346 (M++1).

Workup

  1. waitat 45° C. for 3 h
  2. customThe solvent is removed by rotary evaporation
  3. customthe residue crystallized from dichloromethane and Et2O

Sources & evidence

ORD record
ord-19a481c5245b45ac9f214f24542d6bbe
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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