Triethylamine → 2-(4-Methylpiperidin-1-yl)ethan-1-ol

HRID 1522855Notes

Reaction equation

HRID 1522855 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH2:9][CH2:10][OH:11].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:9][CH2:10][OH:11])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 693814-Methylpiperidine

Product 1

HCID 126346052-(4-Methylpiperidin-1-yl)ethan-1-olYield 20.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4-methylpiperidine (10 g, 0.10 mol), 2-bromoethanol (12.5 g, 0.10 mol), and triethylamine (15 g, 0.15 mol) in CHCl3 (100 mL) was stirred at room temperature for two days. The mixture was concentrated, and the residue was purified on a silica gel column (eluting with NH3—H2O/MeOH/DCM=1/6/300) to give 2-(4-methylpiperidin-1-yl)ethanol (3 g) as a colorless oil. 1H NMR (CDCl3): δ 3.57 (m, 2H), 3.24 (br s, 1H), 2.84 (m, 2H), 2.47 (m, 2H), 2.00 (dt, 2H), 1.58 (m, 2H), 1.35 (m, 1H), 1.21 (dt, 2H), 0.89 (d, 3H); LCMS: 144 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified on a silica gel column (eluting with NH3—H2O/MeOH/DCM=1/6/300)

Sources & evidence

ORD record
ord-af4d3e09289a4911874ea8c44eeff476
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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