Hydrochloric Acid → HCID 20378670, compound

HRID 1390365Notes

Reaction equation

HRID 1390365 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH:4]([C:17]([OH:19])=O)[CH2:3]1.C(=O)(O)[O-].[K+].[H][H].Cl>[Ni].C(O)C.O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]2[C:8]3[C:9]([NH:14][C:17](=[O:19])[CH:4]2[CH2:3]1)=[CH:10][CH:11]=[CH:12][CH:13]=3

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516893Potassium BicarbonateHCID 203786594-Methyl-1-(2-nitrophenyl)piperazine-2-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 20378670HCID 20378670, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 3.5 g. (0.0135 mole) of 4-methyl-1-(o-nitrophenyl)piperazine-2-carboxylic acid, 2.5 g. (0.025 mole) of potassium bicarbonate, 110 ml. of water, 110 ml. of ethanol and 21/2 teaspoons of Raney nickel is hydrogenated in a Parr apparatus for 12 hours at an initial hydrogen pressure of 47 p.s.i. The catalyst is filtered and the filtrate is acidified with dilute hydrochloric acid. The mixture is then basified with sodium hydroxide and extracted with ethylacetate. The extract is dried and concentrated to give 2.3 g. of product. This is treated with 1 equivalent of hydrogen chloride in ethanol. After standing and cooling, filtration gives 2.4 g. of product, as the hydrochloride salt, m.p. 272°-275°. Recrystallization of the salt from ethanol-water gives 1.75 g., m.p. 284°-285° dec.

Workup

  1. additionA mixture of 3.5 g
  2. filtrationThe catalyst is filtered
  3. extractionextracted with ethylacetate
  4. customThe extract is dried
  5. concentrationconcentrated
  6. customto give 2.3 g
  7. temperaturecooling
  8. filtrationfiltration
  9. customgives 2.4 g
  10. customRecrystallization of the salt from ethanol-water
  11. customgives 1.75 g

Sources & evidence

ORD record
ord-187c37c1d863497ab173ba520a58eaa9
Source dataset
uspto-grants-1979_02
Patent number
US04138567

Reaction notes

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