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

HRID 2053521Notes

Reaction equation

HRID 2053521 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, 1H), 8.54 (s, 1H), 7.45 (m, 1H), 7.15-6.90 (m, 6H), 6.90-6.70 (m, 4H), 5.18 (s, 2H), 3.35-3.10 (m, 2H), 1.90-1.65 (m, 5H), 1.40-0.90 (m, 6H); 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-874bcab242fb4b0bb5be991f9c59d9f1
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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