1-(4-Bromophenyl)piperidin-4-ol → 1-(4-Bromophenyl)piperidin-4-yl acetate

HRID 1466267Notes

Reaction equation

HRID 1466267 reaction equation
[C:1]([O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13]N=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].Br[C:19]1C=CC(N2CCC(O)CC2)=CC=1>>[C:1]([O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:19]=[CH:13][C:14]([Br:17])=[CH:15][CH:16]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 235052161-(4-Bromophenyl)piperidin-4-olHCID 667304631-(5-Bromopyridin-2-yl)piperidin-4-yl acetate

Product 1

HCID 667303361-(4-Bromophenyl)piperidin-4-yl acetateYield 92%

Procedure

The title compound was synthesized according to the method described for the synthesis of 1-(5-bromopyridin-2-yl)piperidin-4-yl acetate, except substituting 1-(4-bromophenyl)piperidin-4-ol (606 mg, 2.37 mmol). Crude product was purified by flash chromatography using EtOAc/hexanes as eluent (1:9 to 1:4) to give the title compound as a white solid (648 mg, 92%). 1H NMR (400 MHz, CDCl3) δ 7.33 (d, J=9.0 Hz, 2H), 6.80 (d, J=9.0 Hz, 2H), 4.92-4.89 (m, 1H), 3.47-3.41 (m, 2H), 3.06-3.00 (m, 2H), 2.08 (s, 3H), 2.04-1.99 (m, 2H), 1.84-1.76 (m, 2H); MS ESI 297.9 [M+H]+, calcd for [C13H16BrNO2+H]+ 298.04.

Workup

  1. customThe title compound was synthesized
  2. customCrude product was purified by flash chromatography

Sources & evidence

ORD record
ord-7a34f8bb71e7485d8514538f16612e3b
Source dataset
uspto-grants-2015_04
Patent number
US08999968B2

Reaction notes

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