Potassium Carbonate → Tert-butyl 4-(2-chlorophenylthio)piperidine-1-carboxylate

HRID 2356223

Reaction equation

HRID 2356223 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[SH:26].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[Cl-].[Na+].O>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 80599o-ChlorothiophenolHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 58724129Tert-butyl 4-(2-chlorophenylthio)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
75 °C

Procedure

Tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (2.00 g, 7.16 mmol, prepared according to Blurton et al., WO 00/43362), 2-chlorobenzenethiol (0.898 ml, 7.88 mmol), and potassium carbonate (1.58 g, 11.5 mmol) were stirred together in acetonitrile (15 ml). The reaction was heated to 75° C. and was stirred at that temperature for 15 h. After cooling to room temperature, brine was added, and the mixture was extracted with EtOAc three times. Combined organic layers were dried over MgSO4, filtered and concentrated in vacuo.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc three times
  3. dry with materialCombined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cc7da808700437b9b7daf0a7c8d0497
Source dataset
uspto-grants-2010_07
Patent number
US07759339B2

Linked notes

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