Hydrazine hydrate (1:1) → 1-(Pyridin-2-yl)piperidine-4-carbohydrazide

HRID 269734Notes

Reaction equation

HRID 269734 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=O)C.O.[NH2:19][NH2:20]>CO>[N:9]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:10][CH2:11][CH:6]([C:4]([NH:19][NH2:20])=[O:3])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 38156184-Piperidinecarboxylic acid, 1-(2-pyridinyl)-, ethyl ester

Product 1

HCID 235440481-(Pyridin-2-yl)piperidine-4-carbohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,4,5,6-Tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester (35 g, 150 mmol) (see reference Farmaco, 1993, 48(10), 1439) was dissolved in methanol (700 mL) containing hydrazine hydrate (34 mL, 150 mmol) and was heated under reflux for 18 hours. After this time, more hydrazine hydrate (22.7 mL, 100 mmol) was added and the mixture stirred for a further 18 hours. The mixture was cooled to room temperature and evaporated under reduced pressure. The solid formed was triturated with ethyl acetate to give the title compound as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customevaporated under reduced pressure
  4. customThe solid formed
  5. customwas triturated with ethyl acetate

Sources & evidence

ORD record
ord-91b6afd42fe54328a546719c646703e3
Source dataset
uspto-grants-2008_11
Patent number
US07449462B2

Reaction notes

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