1-Bromo-2-Chloroethane → Ethyl 1-(2-chloroethyl)-3-piperidinecarboxylate

HRID 415324Notes

Reaction equation

HRID 415324 reaction equation
Cl.[CH2:2]([O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][NH2+:9][CH2:8]1)=[O:6])[CH3:3].Br[CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:16][CH2:15][CH2:14][N:9]1[CH2:10][CH2:11][CH2:12][CH:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH2:8]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 86633098HCID 86633098, compound

Product 1

HCID 15076314Ethyl 1-(2-chloroethyl)-3-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-(ethoxycarbonyl)piperidinium hydrochloride (10 g, 65 mmol) in acetone was treated with 1-bromo-2-chloroethane (14.7 g, 0.1 mol) and anhydrous potassium carbonate (13.8 g, 0.1 mol) and the mixture stirred at room temperature for 24 h, the mixture was concentrated and the reside was treated with water and extracted with ether. The extracts were combined and concentrated and the crude was purified by chromatography (silica gel, ethyl acetate:petroleum ether 1:5) to give ethyl 1-(2-chloroethyl)piperidine-3-carboxylate. (3.73 g, Y: 26%). 1HNMR (400 MHz, CDCl3); δ: 1.25 (t, J=7 Hz, 3H), 1.40-3.10 (m, 11H), 3.58 (t, J=7 Hz, 2H), 4.15 (q, 2H). LC-MS (ESI) (m/z): 220 (M+1)+.

Workup

  1. concentrationthe mixture was concentrated
  2. additionthe reside was treated with water
  3. extractionextracted with ether
  4. concentrationconcentrated
  5. customthe crude was purified by chromatography (silica gel, ethyl acetate:petroleum ether 1:5)

Sources & evidence

ORD record
ord-babf51d008344dafb8ada510e4411365
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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