HCID 15337059, compound → HCID 9861313, compound

HRID 1457806Notes

Reaction equation

HRID 1457806 reaction equation
[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

Participants

3

Reactant 1

HCID 15337059HCID 15337059, compound

Product 1

HCID 9861313HCID 9861313, compoundYield 114.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-f5c7e3c50de54868964eeed452cd07d8
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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