Hydrochloric Acid → HCID 22691110, compound

HRID 2164882Notes

Reaction equation

HRID 2164882 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 were 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 were 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-ba0aa60d705345be9ee7fa4908cd3359
Source dataset
uspto-grants-1985_03
Patent number
US04507297

Reaction notes

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