Ethyl chloroformate → Ethyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 2106648Notes

Reaction equation

HRID 2106648 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(Cl)(Cl)Cl.O>[OH:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 24191744(Piperidin-4-yl)methanol--hydrogen chloride (1/1)

Product 1

HCID 19773576Ethyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Conditions

Temperature
20 °C

Procedure

168.3 g (1.22 mol) of potassium carbonate are added to a solution of 61.6 g (406 mmol) of 4-piperidinemethanol hydrochloride in a mixture of 406 ml of chloroform and 406 ml of water, followed by 42.55 ml (440 mmol) of ethyl chloroformate dissolved in 160 ml of chloroform. The mixture is stirred for 3 h at 20° C., the organic phase is separated off, the aqueous phase is extracted with dichloromethane, the organic phases are combined to form a single phase, washed with water and dried over magnesium sulphate, and the solvents are evaporated off under reduced pressure. 76 g of an oil is obtained, this being used without further treatment in the following stage.

Workup

  1. customthe organic phase is separated off
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. customto form a single phase
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customthe solvents are evaporated off under reduced pressure

Sources & evidence

ORD record
ord-6f6469db1ac847fb9c1db74b98387df3
Source dataset
uspto-grants-1990_06
Patent number
US04931449

Reaction notes

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