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

HRID 18728Notes

Reaction equation

HRID 18728 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][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=O)(C)(C)C>CCOC(C)=O>[ClH:1].[C:14]1([C@H:13]2[C@@H:12]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:11][C:10]([NH:26][CH2:27][CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)=[N:9]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68567695tert-butyl (4S,5R)-2-(cyclohexylmethylamino)-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate

Product 1

HCID 68567010(4S,5R)-N-(cyclohexylmethyl)-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 79 (0.23 g, 0.53 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 triturated with Et2O. The insoluble material is filtered to give 89 mg of the product 80. 1H NMR (DMSO-d6) δ 9.08 (m, 1 H), 8.54 (s, 1 H), 7.45 (m, 1 H), 7.15-6.90 (m, 6 H), 6.90-6.70 (m, 4 H), 5.18 (s, 2 H), 3.35-3.10 (m, 2 H), 1.90-1.65 (m, 5 H), 1.40-0.90 (m, 6 H); MS: m/z 334 (M++1).

Workup

  1. customThe solvent is removed by rotary evaporation
  2. customthe residue triturated with Et2O
  3. filtrationThe insoluble material is filtered

Sources & evidence

ORD record
ord-80fa64abfaa24a2c868aa718b59c494e
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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