Hydrazine hydrate (1:1) → HCID 89443858, compound

HRID 2274942Notes

Reaction equation

HRID 2274942 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=O)[CH:6]([C:11]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])=O)[CH2:5]1)(=[O:3])[CH3:2].O.[NH2:22][NH2:23]>C(O)C>[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[NH:22][N:23]=[C:11]([C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[C:16]#[N:17])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 89443863HCID 89443863, compound

Product 1

HCID 89443858HCID 89443858, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-(1-Acetyl-4-oxo-piperidine-3-carbonyl)-benzonitrile (2a) (8 g, 29.6 mmol) in ethanol (26 ml) at 10° C. hydrazine hydrate (4.44 g, 88.8 mmol) was added slowly within 5 min. The mixture was stirred 3 h and allowed to warm to room temperature overnight. The mixture was concentrated to ¼ of its volume until a precipitate formed. The suspension was stirred for 2 h, cooled down and filtrated. The solid was washed with a small amount of ethanol. A second portion of product precipitated overnight from the filtrate and was pooled with the first portion of solid to give 4.02 g of 3-(5-Acetyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-benzonitrile (3a) as a solid.

Workup

  1. additionwas added slowly within 5 min
  2. concentrationThe mixture was concentrated
  3. customformed
  4. stirringThe suspension was stirred for 2 h
  5. temperaturecooled down
  6. filtrationfiltrated
  7. washThe solid was washed with a small amount of ethanol
  8. customA second portion of product precipitated overnight from the filtrate

Sources & evidence

ORD record
ord-49ad538c4d194572af3adb3e94daaa76
Source dataset
uspto-grants-2015_09
Patent number
US09127001B2

Reaction notes

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