Methanol → HCID 22993438, compound

HRID 1275234Notes

Reaction equation

HRID 1275234 reaction equation
[C:1]([C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][CH2:7][N:6]([C:9]2C(CC(O)C)=CC=C3C([NH:14][C:15](=O)[C:10]=23)=O)[CH2:5][CH2:4]1)#[N:2].NN.C[OH:33]>>[C:1]([C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][CH2:7][N:6]([CH2:9][CH:10]([OH:33])[CH2:15][NH2:14])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 22993555HCID 22993555, compound

Product 1

HCID 22993438HCID 22993438, compoundYield 94%

Procedure

A mixture of 3-(4-cyano-4-phenylpiperidin-1-yl)-(2-hydroxypropyl)phthalimide (10 g, 23.48 mmol) and hydrazine (6.01 g, 188 mmol, 8 eq.) in methanol (100 mL) was stirred and refluxed for 4.5 h. It was cooled, filtered, and the solid was washed with methanol (30 mL). Evaporation of solvent from the filtrate gave the product as a viscous oil (5.53 g, 94%).

Workup

  1. temperaturerefluxed for 4.5 h
  2. temperatureIt was cooled
  3. filtrationfiltered
  4. washthe solid was washed with methanol (30 mL)
  5. customEvaporation of solvent from the filtrate

Sources & evidence

ORD record
ord-43024d1c9d4c45b6b58071ce49b93185
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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