Hydrochloric Acid → Ethyl 2-(3-(4-aminophenyl)cyclohexyl)acetate

HRID 1713847Notes

Reaction equation

HRID 1713847 reaction equation
Cl.C1(C(=[N:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH:24]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:23]3)=[CH:18][CH:17]=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CCO>[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH:22]2[CH2:27][CH2:26][CH2:25][CH:24]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:23]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 59464258Ethyl (3-{4-[(diphenylmethylene)amino]phenyl}cyclohexyl)acetate

Product 1

HCID 59464273Ethyl 2-(3-(4-aminophenyl)cyclohexyl)acetateYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous HCl (1 mL of a 1M solution) was added to ethyl (3-{4-[(diphenylmethylene)amino]phenyl}cyclohexyl)acetate (137 mg, 0.32 mmol) in EtOH (10 mL) with stirring. After 1 h the reaction mixture was basified with aqueous potassium carbonate (10 mL of a saturated solution and the mixture was extracted with Et2O (2×15 mL), washed with water (15 mL) and dried. Volatile material was removed by evaporation and the residue was purified by chromatography eluting with 0-35% EtOAc/isohexane to give the title compound (Intermediate 89) (40 mg, 48%) as a gum; MS m/e MH+ 262.

Workup

  1. extraction(10 mL of a saturated solution and the mixture was extracted with Et2O (2×15 mL)
  2. washwashed with water (15 mL)
  3. customdried
  4. customVolatile material was removed by evaporation
  5. customthe residue was purified by chromatography
  6. washeluting with 0-35% EtOAc/isohexane

Sources & evidence

ORD record
ord-bc11850f66a84658aaaf9a8c252f446e
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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