Water → 2,3,4,4a-Tetrahydro-8-(trifluoromethyl)-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one

HRID 2052117Notes

Reaction equation

HRID 2052117 reaction equation
C([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=2[N+:27]([O-])=O)[CH:13]([C:30]([OH:32])=O)[CH2:12]1)(OCC1C=CC=CC=1)=O.C(=O)(O)[O-].[K+].O>[Ni].C(O)C>[F:24][C:23]([F:26])([F:25])[C:20]1[CH:19]=[C:18]2[C:17](=[CH:22][CH:21]=1)[N:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH:13]1[C:30](=[O:32])[NH:27]2

Participants

6

Reactant 3

HCID 962WaterHCID 516893Potassium BicarbonateHCID 20378663HCID 20378663, compound

Product 1

HCID 203394142,3,4,4a-Tetrahydro-8-(trifluoromethyl)-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 7.5 g. of 4-carbobenzoxy-1-(4-trifluoromethyl-2-nitrophenyl)piperazine-2-carboxylic acid, 4.0 g. of potassium bicarbonate, 150 ml. of water and 50 ml. of ethanol is hydrogenated over three teaspoons of Raney nickel catalyst at 50 p.s.i. for 45 minutes. The catalyst is filtered and the filtrate is acidified and extracted with ethylacetate. The aqueous phase is then basified with dilute sodium hydroxide and extracted with ethyl acetate. Concentration of the organic phase gives 1.2 g. of pale yellow solid product, m.p. 193°-195°. This solid is converted to its hydrogen chloride salt in ethanol giving 0.78 g., m.p. 275°-277° dec.

Workup

  1. filtrationThe catalyst is filtered
  2. extractionextracted with ethylacetate
  3. extractionextracted with ethyl acetate
  4. customConcentration of the organic phase gives 1.2 g

Sources & evidence

ORD record
ord-87aa16991dcd489b8e1f6999713cbd99
Source dataset
uspto-grants-1980_01
Patent number
US04182872

Reaction notes

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