2,2,2-Trifluoroethylhydrazine → 3,3a,4,5,6,7-Hexahydro-5-methyl-3-phenyl-7-(phenylmethylene)-2-(2,2,2-trifluoroethyl)-2H-pyrazolo[4,3-c]pyridine, hydrochloride

HRID 462253

Reaction equation

HRID 462253 reaction equation
[ClH:1].[CH:2](=[C:9]1[C:14](=O)[C:13](=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][N:11]([CH3:23])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:24][C:25]([F:30])([F:29])[CH2:26][NH:27][NH2:28]>CO>[ClH:1].[CH3:23][N:11]1[CH2:10][C:9](=[CH:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:14]2=[N:28][N:27]([CH2:26][C:25]([F:30])([F:29])[F:24])[CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]2[CH2:12]1

Participants

4

Reactant 2

HCID 787402,2,2-TrifluoroethylhydrazineHCID 3587084-Piperidinone, 1-methyl-3,5-bis(phenylmethylene)-, hydrochloride

Product 1

HCID 1317109923,3a,4,5,6,7-Hexahydro-5-methyl-3-phenyl-7-(phenylmethylene)-2-(2,2,2-trifluoroethyl)-2H-pyrazolo[4,3-c]pyridine, hydrochlorideYield 59.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred suspension of 12.5 g of 3,5-dibenzylidene-1-methyl-4-piperidone, hydrochloride in 225 ml of methanol is treated with 6.9 g of 70% aqueous 2,2,2-trifluoroethylhydrazine, heated, and the resulting solution refluxed for four hours. The solvent is removed on a rotary evaporator and the light yellow foamy residue (18 g) is dissolved in 90 ml of acetonitrile and treated with 7.5 ml of 5.1 N alcoholic hydrogen chloride; the solid salt rapidly separates after a few seconds. Following cooling for about 16 hours, the material is filtered under nitrogen, washed with cold acetonitrile and ether, and dried in vacuo yielding 9.7 g of material, melting point 185°-187° C (foaming); sintering at 181° C. Crystallization from 50 ml of methanol and 50 ml of ether yields 7.9 g of product, melting point 185°-187° C (foaming).

Workup

  1. temperatureheated
  2. temperaturethe resulting solution refluxed for four hours
  3. customThe solvent is removed on a rotary evaporator
  4. dissolutionthe light yellow foamy residue (18 g) is dissolved in 90 ml of acetonitrile
  5. additiontreated with 7.5 ml of 5.1 N alcoholic hydrogen chloride
  6. waitthe solid salt rapidly separates after a few seconds
  7. temperatureFollowing cooling for about 16 hours
  8. filtrationthe material is filtered under nitrogen
  9. washwashed with cold acetonitrile and ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-18ca2828380f46eea17a64b306636fae
Source dataset
uspto-grants-1977_12
Patent number
US04065617

Linked notes

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