Ethanolamine → N-(2-Hydroxyethyl)piperidine-4-carboximidic acid

HRID 1389157Notes

Reaction equation

HRID 1389157 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:22])[NH:18][CH2:19][CH2:20][OH:21])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(OC(N1CCC(C(Cl)=O)CC1)=O)C1C=CC=CC=1.OCCN>>[OH:21][CH2:20][CH2:19][NH:18][C:17]([CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)=[O:22]

Participants

4

Reactant 3

HCID 700EthanolamineHCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylateHCID 20298124HCID 20298124, compound

Product 1

HCID 2760458N-(2-Hydroxyethyl)piperidine-4-carboximidic acid

Procedure

1-Benzyloxycarbonyl-4-[N-(2-hydroxyethyl)carbamoyl]piperidine [6.24 g, m.p. 107°-108°, Found: C, 62.8; H, 7.2; N, 9.0; Calculated: C, 62.7; H, 7.2; N, 9.1; prepared similarly to Preparation C but starting from 1-benzyloxycarbonylpiperidine-4-carboxylic acid chloride and 2-hydroxyethylamine] was hydrogenated as in Preparation G to give 4-[N-(2-hydroxyethyl)carbamoyl]piperidine. The i.r. and n.m.r. spectra were consistent with this structure and the product was used in Example 6 without further purification.

Workup

  1. customprepared similarly to Preparation C
  2. customwas hydrogenated as in Preparation G

Sources & evidence

ORD record
ord-800214de9e04481aa92ee7ff57d0c805
Source dataset
uspto-grants-1981_01
Patent number
US04243666

Reaction notes

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