Hydrogen chloride-ethyl acetate → 4-(Acetylthio)piperidine hydrochloride

HRID 381425

Reaction equation

HRID 381425 reaction equation
[C:1]([S:4][CH:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].C(OCC)(=O)C.[ClH:24]>C(OCC)(=O)C>[ClH:24].[C:1]([S:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 22494773tert-Butyl 4-(acetylthio)piperidine-1-carboxylate

Product 1

HCID 183632904-(Acetylthio)piperidine hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

In 45 ml of ethyl acetate were dissolved 1.25 g (4.82 mmol) of 4-(acetylthio)-1-(tert-butoxycarbonyl)piperdine as described in Reference example 11, and 12.0 ml (48.2 mmol) of a 4N hydrogen chloride-ethyl acetate solution were added to the solution, followed by stirring of the resulting mixture at 50° C. for 4 hours. After cooling, the precipitated solid was collected by filtration and washed with hexane to obtain 885 mg (yield: 94%) of the desired compound as a slightly yellow powder.

Workup

  1. additionwere added to the solution
  2. temperatureAfter cooling
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with hexane

Sources & evidence

ORD record
ord-6c1c4656a7cd48f4adc4a61e0e02642c
Source dataset
uspto-grants-2001_10
Patent number
US06306880B1

Linked notes

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