Hydrazine hydrate (1:1) → 2,2,6,6-Tetramethyl-4-hydroxypiperidine-4-carboxylic acid hydrazide

HRID 27794Notes

Reaction equation

HRID 27794 reaction equation
C[O:2][C:3]([C:5]1([OH:15])[CH2:10][C:9]([CH3:12])([CH3:11])[NH:8][C:7]([CH3:14])([CH3:13])[CH2:6]1)=O.O.[NH2:17][NH2:18]>CO>[CH3:11][C:9]1([CH3:12])[CH2:10][C:5]([OH:15])([C:3]([NH:17][NH2:18])=[O:2])[CH2:6][C:7]([CH3:14])([CH3:13])[NH:8]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1066914-Piperidinecarboxylic acid, 4-hydroxy-2,2,6,6-tetramethyl-, methyl ester

Product 1

HCID 705934412,2,6,6-Tetramethyl-4-hydroxypiperidine-4-carboxylic acid hydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

16.2 parts of 2,2,6,6-tetramethyl-4-hydroxypiperidine-4-carboxylic acid methyl ester (according to German Patent No. 91,122), 5 parts of hydrazine hydrate and 20 parts of methanol were boiled under reflux for 10 hours and the methanol was subsequently distilled off. The residue was recrystallised from cyclohexane. Yield: 15.3 parts of 2,2,6,6-tetramethyl-4-hydroxypiperidine-4-carboxylic acid hydrazide melting at 121° to 123° C.

Workup

  1. temperatureunder reflux for 10 hours
  2. distillationthe methanol was subsequently distilled off
  3. customThe residue was recrystallised from cyclohexane

Sources & evidence

ORD record
ord-e4085b9eb67d4f9b9c36c9dc0f2f17de
Source dataset
uspto-grants-1980_09
Patent number
US04223147

Reaction notes

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