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

HRID 462260

Reaction equation

HRID 462260 reaction equation
Cl.[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]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:31][C:32]([F:37])([F:36])[CH2:33][NH:34][NH2:35]>CO>[C:3]1([CH:2]2[CH:9]3[CH2:10][N:11]([CH2:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:12][C:13](=[CH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:14]3=[N:35][N:34]2[CH2:33][C:32]([F:37])([F:36])[F:31])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 787402,2,2-TrifluoroethylhydrazineHCID 681188373,5-Dibenzylidene-1-(2-phenylethyl)-4-piperidone monohydrochloride

Product 1

HCID 541622763,3a,4,5,6,7-Hexahydro-3-phenyl-5-(2-phenylethyl)-7-(phenylmethylene)-2-(2,2,2-trifluoroethyl)-2H-pyrazolo-[4,3-c]pyridineYield 114.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ten grams of 3,5-dibenzylidene-1-(2-phenylethyl)-4-piperidone monohydrochloride and 4.4 g of 70% aqueous 2,2,2-trifluoroethylhydrazine are reacted in 150 ml of methanol at reflux for 4 hours. The solvent is removed on a rotary evaporator leaving 13.1 g of brittle residue. The material is converted to 10.7 g of free base using potassium carbonate and ether extractions. The free base is dissolved in 50 ml of warm isopropyl ether and diluted with 20 ml of hexane. After the solution is cooled to room temperature, seeded and rubbed, the crystalline base gradually separates. After cooling overnight, the solid is filtered, washed with cold 5:2 isopropyl ether-hexane and dried to yield 3.6 g of product, melting point 113°-114° C, sintering at 105° C.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-a82c7c886fe04636837b8f994ce3f46d
Source dataset
uspto-grants-1977_12
Patent number
US04065617

Linked notes

Loading…