Acetic Acid → 1-Benzylpiperidine-4-thiol

HRID 1742629Notes

Reaction equation

HRID 1742629 reaction equation
N=C1N(CC[S:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)C2C=CC(OC(F)(F)F)=CC=2S1.C(N1CCC(SC(=O)C)CC1)C1C=CC=CC=1.C(O)(=O)C.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>[OH-].[Na+]>[CH2:16]([N:13]1[CH2:14][CH2:15][CH:10]([SH:9])[CH2:11][CH2:12]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6097028Ammonium SulfateHCID 151664202-Imino-3-{2-[(1-benzyl-4-piperidyl)thio]ethyl}-6-trifluoromethoxybenzothiazolineHCID 151664211-Benzyl-4-acetylthiopiperidine

Product 1

HCID 112757831-Benzylpiperidine-4-thiol

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The 1-benzyl-4-mercaptopiperidine may be prepared in the following manner: 8 g of 1-benzyl-4-acetylthiopiperidine dissolved in 85 cm3 of a 6% aqueous solution of sodium hydroxide are stirred under a nitrogen stream for 16 hours. 10 cm3 of acetic acid and 57.5 g of ammonium sulphate are added to this solution. The mixture is then extracted with two times 100 cm3 of diethyl ether and the organic phase is dried over anhydrous magnesium sulphate and concentrated to dryness at 40° C. under reduced pressure (20 mm of mercury; 2.7 kPa). 5.5 g of 1-benzyl-4-mercaptopiperidine are thus directly isolated in the form of an oil which is used as it is in subsequent synthesis.

Workup

  1. extractionThe mixture is then extracted with two times 100 cm3 of diethyl ether
  2. dry with materialthe organic phase is dried over anhydrous magnesium sulphate
  3. concentrationconcentrated to dryness at 40° C. under reduced pressure (20 mm of mercury; 2.7 kPa)

Sources & evidence

ORD record
ord-4cb5f25197e24a0bb27ecf95c4cf1cb1
Source dataset
uspto-grants-1994_08
Patent number
US05340824

Reaction notes

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