Ethanolamine → 1-Methyl-N-(2-hydroxyethyl)-piperidine-4-carboxylic acid amide

HRID 1198147Notes

Reaction equation

HRID 1198147 reaction equation
C(O[C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1)=[O:5])C.[OH:13][CH2:14][CH2:15][NH2:16]>C(Cl)Cl.CO>[CH3:12][N:9]1[CH2:8][CH2:7][CH:6]([C:4]([NH:16][CH2:15][CH2:14][OH:13])=[O:5])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 11062856Ethyl 1-methylpiperidine-4-carboxylate

Product 1

HCID 150688501-Methyl-N-(2-hydroxyethyl)-piperidine-4-carboxylic acid amideYield 52%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
60 °C

Procedure

17.1 g. (0.1 mole) 1-Methylpiperidine-4-carboxylic acid ethyl ester (literature: J.A.C.S., 74, 3831/1952). are heated to 60° C. for 48 hours with 9 ml. (0.15 mole) 2-hydroxyethylamine and purified over a silica gel column with methylene chloride/methanol (9:1 v/v). There are obtained 9.5 g. of base in the form of a viscous oil. Yield 52% of theory.

Workup

  1. customThere are obtained 9.5 g

Sources & evidence

ORD record
ord-a98fb4dd781e47c7b6c27cfdeefd3917
Source dataset
uspto-grants-1994_01
Patent number
US05280031

Reaction notes

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