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

HRID 2368901Notes

Reaction equation

HRID 2368901 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-afeaf102fb1e42fb97e916b0d5aaebe4
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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