Reaction #41840

ord-1999f9fd5f3e4b5f818c084473b4137d

Reaction equation

O=Cc1ccc(C(=O)N2CCN(C3CC3)CC2)cc1
4-(4-cyclopropyl-piperazine-1-carbonyl)-benzaldehyde
CC#N
acetonitrile
O=S([O-])O.[Na+]
NaHSO3
O=C(c1ccc(C(O)S(=O)(=O)[O-])cc1)N1CCN(C2CC2)CC1.[Na+]
Sodium [4-(4-Cyclopropyl-piperazine-1-carbonyl)-phenyl]-hydroxy-methanesulfonate

Solvents

Conditions

Temperature
50°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe reaction mixture was then cooled to 17° C
  2. 2
    FiltrationThe product was collected by filtration as a white solid

Procedure

A 100 mL flask was charged with 4-(4-cyclopropyl-piperazine-1-carbonyl)-benzaldehyde (2.58 g, 10.0 mmol, 1.0 eq), acetonitrile (30 mL), and water (1.0 mL) under nitrogen atmosphere. The reaction mixture was heated to 50° C. A solution of NaHSO3 (1.14 g, 11.0 mol, 1.1 eq) in water (2.0 mL) was added dropwise over 5 min. The reaction mixture was then cooled to 17° C. The product was collected by filtration as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728129B2uspto-grants-2010_06