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

HRID 6915Notes

Reaction equation

HRID 6915 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)HCID 38156184-Piperidinecarboxylic acid, 1-(2-pyridinyl)-, ethyl ester

Product 1

HCID 235440481-(Pyridin-2-yl)piperidine-4-carbohydrazideYield 52.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,4,5,6-Tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester (1 g, 4.3 mmol)(see reference Farmaco, 1993, 48(10), 1439) was dissolved in methanol (20 ml) containing hydrazine hydrate (620 μl, 20 mmol) and was heated under reflux for 18 hours. The mixture was cooled to room temperature and evaporated under reduced pressure. The solid formed was triturated with propan-2-ol to give the title compound as a white solid (493 mg).

Workup

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

Sources & evidence

ORD record
ord-082ae31a954c4fd782ac740e11e1b426
Source dataset
uspto-grants-2006_08
Patent number
US07084145B2

Reaction notes

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