Hydrochloric Acid → trans-6-(2-Chlorophenyl)cyclohex-3-en-1-amine

HRID 1172320Notes

Reaction equation

HRID 1172320 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C@H:13]([N+:14]([O-])=O)[CH2:12][CH:11]=[CH:10][CH2:9]1.Cl.C([O-])(O)=O.[Na+]>CO.[Zn]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C@H:13]([NH2:14])[CH2:12][CH:11]=[CH:10][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68771799HCID 68771799, compound

Product 1

HCID 68772117trans-6-(2-Chlorophenyl)cyclohex-3-en-1-amine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of Example 1A (100 mg, 0.042 mmol) in a 2 mL solution of 1:1 aqueous concentrated HCl in methanol at 0° C., Zn dust (32 mg, 0.5 mmol) was added in several portions. The solution was allowed to warm to room temperature over three hours. Afterwards, the solution was carefully basified with saturated NaHCO3. The mixture was extracted with ethyl acetate, concentrated, taken up in dichloromethane, and filtered through Celite. Concentration of the filtrate gave the title compound. 1H NMR (300 MHz, C5D5N) δ ppm 7.41-7.43 (m, 2H), 7.24-7.28 (m, 1H), 7.12-7.14 (m, 1H), 5.70-5.73 (m, 2H), 3.49-3.54 (m, 2H), 2.55-2.58 (m, 1H), 2.37-2.41 (m, 1H), 2.14-2.24 (m, 2H). MS (ESI+) m/z 208 (M+H)+

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. concentrationconcentrated
  3. filtrationfiltered through Celite

Sources & evidence

ORD record
ord-ab50b131a7394623a7e4964f9d1534f1
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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