p-Toluenesulfonic acid → 2-(1-Benzylpiperidin-4-yl)-5-bromobenzo[d]oxazole

HRID 710085Notes

Reaction equation

HRID 710085 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][C:17]2[CH:22]=[C:21]([Br:23])[CH:20]=[CH:19][C:18]=2[OH:24])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[O:24][C:18]3[CH:19]=[CH:20][C:21]([Br:23])=[CH:22][C:17]=3[N:16]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 711141861-benzyl-N-(5-bromo-2-hydroxyphenyl)piperidine-4-carboxamide

Product 1

HCID 711141872-(1-Benzylpiperidin-4-yl)-5-bromobenzo[d]oxazoleYield 24.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Intermediate 22 (47.6 g, 0.122 mol) was dissolved in xylene (500 ml) and added p-Toluenesulphonic acid (46 g, 0.24 mol). This mixture was refluxed for 20 h under a dean-stark condenser. Xylene was removed and pH of the residue was adjusted to 9 using aq NaHCO3 solution. Work up (EtOAc/H2O) afforded the crude. Crude was purified by column on 60-120 mesh silicagel using a gradient mixture of EtOAc and Petether (10:90) as eluent to afford the titled compound (11 g) as brown solid.

Workup

  1. temperatureThis mixture was refluxed for 20 h under a dean-stark condenser
  2. customXylene was removed
  3. customWork up (EtOAc/H2O) afforded the crude
  4. customCrude was purified by column on 60-120 mesh silicagel
  5. additiona gradient mixture of EtOAc and Petether (10:90) as eluent

Sources & evidence

ORD record
ord-0675eb050bb04621ad7564d762611032
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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