HCID 15337059、化合物 → HCID 9861313、化合物

HRID 1457806ノート

反応式

HRID 1457806 の反応式
[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

参加物

3

反応物 1

HCID 15337059HCID 15337059、化合物

生成物 1

HCID 9861313HCID 9861313、化合物収率 114.6%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-f5c7e3c50de54868964eeed452cd07d8
出典データセット
uspto-grants-1998_12
特許番号
US05849765

反応ノート

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