Hydrochloric Acid → HCID 22691110, compound

HRID 1982507Notes

Reaction equation

HRID 1982507 reaction equation
Cl.[CH3:2][CH:3]([CH3:28])[CH2:4][C@H:5]([NH:20]C(=O)OC(C)(C)C)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7]>C(OCC)(=O)C>[NH2:20][C@H:5]([C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])[CH2:4][CH:3]([CH3:2])[CH3:28]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54191163HCID 54191163, compound

Product 1

HCID 22691110HCID 22691110, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under cooling with ice, hydrogen chloride gas was fed and saturated into ethyl acetate (200 ml), and tert-butyl (s)-3-methyl-1-[4-(2-pyridyl)piperazine-1-yl carbonyl]-butylcarbamate (16.0 g) obtained above was added gradually. The mixture was stirred for 30 minutes. The solvent and hydrogen chloride was removed by distillation under reduced pressure, and 200 ml of water was added to the white powder thus obtained to dissolve the powder therein. After washing with ethyl acetate, an aqueous sodium bicarbonate solution was added to bring the pH to 8. Followed by the addition of sodium chloride, extraction with 100 ml of ethyl acetate was repeated three times. After drying over sodium sulfate, the solvent was removed by distillation under reduced pressure to yield 9.16 g of 1-L-leucyl-4-(2-pyridyl)piperazine (yield: 78.0%).

Workup

  1. customobtained
  2. additionabove was added gradually
  3. customThe solvent and hydrogen chloride was removed by distillation under reduced pressure, and 200 ml of water
  4. additionwas added to the white powder
  5. customthus obtained
  6. dissolutionto dissolve the powder
  7. washAfter washing with ethyl acetate
  8. additionan aqueous sodium bicarbonate solution was added
  9. additionFollowed by the addition of sodium chloride, extraction with 100 ml of ethyl acetate
  10. dry with materialAfter drying over sodium sulfate
  11. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-e1510329940f4c24889732bd211a29f7
Source dataset
uspto-grants-1986_06
Patent number
US04596803

Reaction notes

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