Methyl iodide → 4-(4-Bromophenyl)-1-methylpiperidin-4-ol

HRID 2281727Notes

Reaction equation

HRID 2281727 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CI.[C:17]([O-])([O-])=O.[K+].[K+]>CC(C)=O.CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:14])[CH2:9][CH2:10][N:11]([CH3:17])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 939114-(4-Bromophenyl)-4-hydroxypiperidine

Product 1

HCID 106596344-(4-Bromophenyl)-1-methylpiperidin-4-olYield 94.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture of 4-(4-bromophenyl)piperidin-4-ol (1.5 g, 5.9 mmol), methyl iodide (0.4 mL, 6.4 mmol), and K2CO3 (1.2 g, 8.8 mmol) in acetone was stirred at rt for 90 min. The reaction was diluted with EtOAc and water was added. The resulting mixture was extracted with EtOAc and the combined organic extracts were dried over MgSO4 and concentrated to give the title compound as a yellow solid (1.5 g, used without further purification). 1H NMR (400 MHz, CDCl3) δ 7.40 (d, J=8.1 Hz, 2H), 7.29 (d, J=8.1 Hz, 2H), 3.20 (br s, 1H), 2.64-2.61 (m, 2H), 2.39 (t, J=11.8 Hz, 2H), 2.21 (s, 3H), 2.03-1.96 (m, 2H), 1.64-1.61 (m, 2H); MS ESI 270.0 [M+H]+, calcd for [C12H16BrNO+H]+ 270.04.

Workup

  1. additionwas added
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-37232d88cc9d4cd1ac3787a4ee8b5a1d
Source dataset
uspto-grants-2015_09
Patent number
US09139563B2

Reaction notes

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