Divinyl sulfone → 4-[1-(4-Bromo-2-methyl-phenyl)-1-methyl-ethyl]-thiomorpholine 1,1-dioxide

HRID 216711

Reaction equation

HRID 216711 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:11])([CH3:10])[CH3:9])=[C:4]([CH3:12])[CH:3]=1.[CH:13]([S:15]([CH:18]=[CH2:19])(=[O:17])=[O:16])=[CH2:14]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:11]2[CH2:19][CH2:18][S:15](=[O:17])(=[O:16])[CH2:13][CH2:14]2)([CH3:9])[CH3:10])=[C:4]([CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 6496Divinyl sulfoneHCID 593927012-(4-Bromo-2-methylphenyl)propan-2-amine

Product 1

HCID 593926954-[1-(4-Bromo-2-methyl-phenyl)-1-methyl-ethyl]-thiomorpholine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(4-Bromo-2-methyl-phenyl)-1-methyl-ethylamine (preparation 48, 544 mg, 2 mmol), vinyl sulfone (200 μl, 2 mmol) in EtOH (8 ml) is heated to 100° C. for 6 h and then allowed to cool to RT. EtOH is removed under HV and the residue is purified by flash chromatography (silicagel, CH2Cl2:EtOAc=1:0=>0:1) to afford the title compound as a pale pink solid, Rt=1.231 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min); MS: 346 (M+1, 79Br)+.

Workup

  1. customEtOH is removed under HV
  2. customthe residue is purified by flash chromatography (silicagel, CH2Cl2:EtOAc=1:0=>0:1)

Sources & evidence

ORD record
ord-7e2083460f5e4699a97452b03ab024d0
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Linked notes

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