p-Toluenesulfonic acid → 1,5,6,7-tetrahydro-1-(4-bromophenyl]-3-(morpholin-4-yl)-2H-azepin-2-one

HRID 25168Notes

Reaction equation

HRID 25168 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10][C:9]2=[O:16])=[CH:4][CH:3]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][CH:11]=[C:10]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:9]2=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 22566235HCID 22566235, compound

Product 1

HCID 225662551,5,6,7-tetrahydro-1-(4-bromophenyl]-3-(morpholin-4-yl)-2H-azepin-2-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-[4-bromophenyl]-3-oxocaprolactam (1.31 g, 4.63 mmol), morpholine (1.60 mL, 18.52 mmol), and p-toluenesulfonic acid (catalytic amount) were refluxed with 50 mL benzene using a Dean Stark apparatus under N2 for 12 h. The solvent was then removed in vacuo and the residue was dried under vacuum to give 1,5,6,7-tetrahydro-1-[4-bromophenyl]-3-(morpholin-4-yl)-2H-azepin-2-one as a yellow solid. LRMS (AP+): 351.0, 353.0, (M+H)+.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-665a33cc989d486aa027c615fc2cbc05
Source dataset
uspto-grants-2005_02
Patent number
US06858616B2

Reaction notes

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