Phenyl isocyanate → 1-Piperidinecarboxamide

HRID 867723Notes

Reaction equation

HRID 867723 reaction equation
FC(F)(F)C1C=CC(N2C3C(=CC=CC=3)C([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=N2)=CC=1.C1([N:32]=[C:33]=[O:34])C=CC=CC=1>C1(C)C=CC=CC=1>[N:21]1([C:33]([NH2:32])=[O:34])[CH2:20][CH2:19][CH2:18][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 23048179HCID 23048179, compound

Product 1

HCID 728871-Piperidinecarboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 4-[1-[4-(trifluoromethyl)phenyl]-1H-indazol-3-yl]piperidine-1-carbonitrile of Example 77 (15 g, 0.041 moles) and 25% H2SO4 (100 ml) was refluxed for 20 hours. The mixture was cooled, poured into H2O, and basified with a 25% NaOH solution. The product was extracted (dichloromethane), dried (MgSO4), and concentrated to yield 13 g (93%) of 1-[4-(trifluoromethyl)phenyl]-3-(4-piperidinyl)-1H-indazole as an oil. To a stirred suspension of the indazole (4.0 g, 0.012 moles) in toluene (60 ml) was added phenyl isocyanate (1.38 ml, 0.013 moles). The reaction temperature rose to 35° C. and the product precipitated from the solution. The product was collected and recrystallized twice from toluene to yield 3.57 g (66%) of N-phenyl-4-[1-(4-trifluoromethyl)phenyl]-1H-indazol-3-yl]piperidine-1-carboxamide, m.p. 190°-192° C.

Workup

  1. customrose to 35° C.
  2. customthe product precipitated from the solution
  3. customThe product was collected
  4. customrecrystallized twice from toluene

Sources & evidence

ORD record
ord-5a0c2db4a3b845e09d3e80f26912e4d8
Source dataset
uspto-grants-1988_10
Patent number
US04775761

Reaction notes

Loading…