Hydrazine hydrate (1:1) → HCID 178423825, compound

HRID 606771Notes

Reaction equation

HRID 606771 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]#[C:16][C:17](=O)[CH3:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:27][NH2:28]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]2[NH:28][N:27]=[C:17]([CH3:18])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 865943864-(1-Phenyl-1-(3-oxo-1-butyn-1-yl)methylene)-piperidine-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 178423825HCID 178423825, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[1-phenyl-1-(3-oxo-1-butyn-1-yl)methylene]-piperidine-1-carboxylic acid tert-butyl ester (0.365 g, 1.069 mmol) and hydrazine hydrate (0.065 mL, 1.14 mmol) in EtOH (5 mL) was allowed to stir at rt for 2 h and then it was heated at 80° C. for 14 h. The solvent was subsequently removed under reduced pressure and the residue was purified by preparative HPLC affording the title compound (0.151 g, 40%) as a colorless solid

Workup

  1. temperatureit was heated at 80° C. for 14 h
  2. customThe solvent was subsequently removed under reduced pressure
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-93e371648f264e90826124fa79fb387b
Source dataset
uspto-grants-2011_03
Patent number
US07915283B2

Reaction notes

Loading…