Potassium Carbonate → tert-Butyl 4-((4-bromophenyl)thio)piperidine-1-carboxylate

HRID 411507Notes

Reaction equation

HRID 411507 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([S:26][C:23]2[CH:24]=[CH:25][C:20]([Br:19])=[CH:21][CH:22]=2)[CH2:12][CH2:13]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 11760469tert-Butyl 4-((4-bromophenyl)thio)piperidine-1-carboxylateYield 95.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-BOC 4-mesyloxypiperidine (40 g, 0.14 mol), 4-bromothiophenol (32 g, 0.17 mol) and potassium carbonate (30 g, 0.22 mol) were mixed at room temperature in CH3CN (300 ml) and heated at reflux for 18 h. Work-up by partitioning between water and EtOAc afforded 50 g of material as a yellow oil. δH (360 MHz, CDCl3) 1.44 (9H, s), 1.45-1.55 (2H, m), 1.85-1.95 (2H, m), 2.85-2.95 (2H, m), 3.10-3.20 (1H, m), 3.95-4.05 (2H, m), 7.25-7.30 (2H, m), 7.40-7.45 (2H, m).

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. customby partitioning between water and EtOAc

Sources & evidence

ORD record
ord-83fb834fe2c0432192e7b4e1f0e44be8
Source dataset
uspto-grants-2003_05
Patent number
US06559166B1

Reaction notes

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