Phenyl{4-[(phenylsulfanyl)methyl]piperidin-1-yl}methanone → 1-Benzyl-4-phenylsulfanylmethyl-piperidine

HRID 1291198Notes

Reaction equation

HRID 1291198 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([N:9]1[CH2:10][CH2:11][CH:12]([CH2:15][S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 67623230Phenyl{4-[(phenylsulfanyl)methyl]piperidin-1-yl}methanone

Product 1

HCID 189198091-Benzyl-4-phenylsulfanylmethyl-piperidineYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

40 ml (0.04 mol) of 1M BH3 in THF were added to a solution of 3.11 g (0.01 mol) of 1-benzoyl-4-thiophenoxymethyl-piperidine in 50 ml of THF. The mixture was boiled at reflux for 16 hrs. Then, 90 ml of 1N aqueous HCI were added and the mixture was stirred for 1.5 hrs. It was extracted with ether and concentrated and the residue was taken up in a mixture of 20 ml of glacial acetic acid and 20 ml of THF and boiled at reflux for 3 hrs. The solvents were distilled off and the residue was taken up in ethyl acetate, washed with saturated sodium carbonate solution and sodium chloride solution and dried over sodium sulfate. The solvent was removed and the residue was chromatographed on silica gel with ethyl acetate/hexane (1:9) as the eluent. 2.3 g (77%) of 1-benzyl-4-phenylsulfanylmethyl-piperidine were obtained as a colorless oil. MS: me/e=298 (C19H24NS+).

Workup

  1. temperatureat reflux for 16 hrs
  2. additionThen, 90 ml of 1N aqueous HCI were added
  3. extractionIt was extracted with ether
  4. concentrationconcentrated
  5. additionthe residue was taken up in a mixture of 20 ml of glacial acetic acid and 20 ml of THF
  6. temperatureat reflux for 3 hrs
  7. distillationThe solvents were distilled off
  8. washwashed with saturated sodium carbonate solution and sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. customThe solvent was removed
  11. customthe residue was chromatographed on silica gel with ethyl acetate/hexane (1:9) as the eluent

Sources & evidence

ORD record
ord-68a6e88e1049454a8f2b98e344906a93
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

Loading…