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

HRID 1172320노트

반응식

HRID 1172320 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

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)+

후처리

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

출처 및 근거

ORD 기록
ord-ab50b131a7394623a7e4964f9d1534f1
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834012B2

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