Reaction #40710

ord-05e877e49f6e4a7498b3988be9eb552d

Reaction equation

CC(=O)c1ccc(N2CCOCC2)cc1
4-morpholinoacetophenone
COC(OC)N(C)C
N,N-dimethylformamide dimethyl acetal
NN.O
hydrazine hydrate
c1cc(-c2ccc(N3CCOCC3)cc2)n[nH]1
title compound
c1cc(-c2ccc(N3CCOCC3)cc2)n[nH]1
4-[4-(1H-Pyrazol-3-yl)phenyl]morpholine

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas heated
  2. 2
    Temperatureunder reflux for 7 hours
  3. 3
    Temperatureagain heated
  4. 4
    Temperatureunder reflux for about 6 hours
  5. 5
    OtherThe solid formed
  6. 6
    Temperatureon cooling the mixture
  7. 7
    Filtrationwas filtered off with suction
  8. 8
    Washthoroughly washed with methanol

Procedure

A mixture of 2.05 g of 4-morpholinoacetophenone (10 mmol) and N,N-dimethylformamide dimethyl acetal was heated under reflux for 7 hours. The mixture was then mixed with 30 ml of methanol and, after addition of 0.57 ml of hydrazine hydrate, again heated under reflux for about 6 hours. The solid formed on cooling the mixture was filtered off with suction and thoroughly washed with methanol, resulting in 3.8 g of the title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728012B2uspto-grants-2010_06