Morpholine → 4-(1-(4-Bromophenyl)piperidin-4-yl)morpholine

HRID 447308Notes

Reaction equation

HRID 447308 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]([CH3:16])[CH3:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.BrC1C=CC(N2CCC(=O)CC2)=CC=1.N1C[CH2:35][O:34][CH2:33]C1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([N:14]3[CH2:16][CH2:35][O:34][CH2:33][CH2:15]3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 246921481-(4-Bromophenyl)piperidin-4-oneHCID 667303771-(4-bromophenyl)-N,N-dimethylpiperidin-4-amine

Product 1

HCID 667303494-(1-(4-Bromophenyl)piperidin-4-yl)morpholineYield 97%

Procedure

The title compound was synthesized according to the synthesis of 1-(4-bromophenyl)-N,N-dimethylpiperidin-4-amine, except reacting 1-(4-bromophenyl)piperidin-4-one (500 mg, 1.97 mmol) with morpholine (0.21 mL, 2.36 mmol) for 25 h to give the title compound as a yellow solid (620 mg, 97%). 1H NMR (400 MHz, MeOD) δ 7.31 (d, J=8.2 Hz, 2H), 6.89 (d, J=8.6 Hz, 2H), 3.87-3.67 (m, 6H), 2.71 (t, J=12.5 Hz, 2H), 2.67-2.62 (m, 4H), 2.37-2.36 (m, 1H), 2.04-1.97 (m, 2H), 1.72-1.56 (m, 2H); MS ESI 325.2 [M+H]+, calcd for [C15H21BrN2O+H]+ 325.08.

Workup

  1. customThe title compound was synthesized
  2. customfor 25 h

Sources & evidence

ORD record
ord-b1d22621cd8b4d9b8d642127af8d3e56
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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