HCID 15337059, 화합물 → HCID 9861313, 화합물

HRID 1457806노트

반응식

HRID 1457806 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1(O)[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1>FC(F)(F)C(O)=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH:11]=1

참가 물질

3

반응물 1

HCID 15337059HCID 15337059, 화합물

생성물 1

HCID 9861313HCID 9861313, 화합물수율 114.6%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

4-(Benzothiophen-2-yl)-1-benzyl-4-hydroxypiperidine (4.5 g, 0.01 mol) was dissolved in trifluoroacetic acid (50 ml) and stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue partitioned between aqueous saturated potassium carbonate solution and dichloromethane (3×100 ml). The combined organic layers were washed with brine (200 ml), dried (MgSO4) and concentrated. The crude product was purified by flash chromatography eluting with 10% ethyl acetate in petroleum ether. Concentration of the appropriate fractions gave the title compound as a pale yellow solid (3.5 g, 82%); δH (CDCl3), 2.63 (2H, m, NCH2CH2), 2.73 (2H, m, NCH2 CH2), 3.19 (2H, m, NCH2CH2), 3.64 (2H, s, NCH2Ar), 6.19 (1H, m, NCH2CH), 7.11 (1H, s, ArH), 7.31 (7H, m, ArH), 7.65 (1H, d of d, J 6.4Hz, J 1.9Hz, ArH), 7.72 (1H, d of d, J 6.9Hz, J 1.8Hz, ArH). m/z (ES+) 306 (M+1)+.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between aqueous saturated potassium carbonate solution and dichloromethane (3×100 ml)
  3. washThe combined organic layers were washed with brine (200 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography
  7. washeluting with 10% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-f5c7e3c50de54868964eeed452cd07d8
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849765

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