2-Bromoethanol → 2-(4-Aminopiperidin-1-yl)ethan-1-ol

HRID 588048Notes

Reaction equation

HRID 588048 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7]C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.Br[CH2:16][CH2:17][OH:18].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[NH2:7][CH:4]1[CH2:3][CH2:2][N:1]([CH2:16][CH2:17][OH:18])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 157334452-(4-Aminopiperidin-1-yl)ethan-1-olYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.5 g of tert-butyl 4-piperidinylcarbamate, 0.21 ml of 2-bromoethanol and 2.76 g of K2CO3 in 10 ml of acetonitrile was stirred for 5 hrs under reflux. The reaction mixture was cooled to a room temperature, filtered to remove solids, and concentrated. The concentrate was purified by silica gel column chromatography (mobile phase: 20 (v/v) % EA in hexane) to afford 0.58 g of the title compound (Yield: 94%). 1H NMR (CDCl3) δ 4.76 (d, 1H), 3.65 (t, 2H), 3.48 (m, 1H), 2.92 (m, 2H), 2.59 (t, 2H), 2.26 (m, 2H), 1.94 (m, 2H), 1.52 (m, 2H), 1.44 (s, 9H) ppm.

Workup

  1. temperatureunder reflux
  2. filtrationfiltered
  3. customto remove solids
  4. concentrationconcentrated
  5. customThe concentrate was purified by silica gel column chromatography (mobile phase: 20 (v/v) % EA in hexane)

Sources & evidence

ORD record
ord-2eb6565c23a04f4584e68d64af0df513
Source dataset
uspto-grants-2016_01
Patent number
US09227955B2

Reaction notes

Loading…