HCID 21701706, compound → HCID 21701679, compound

HRID 1596211Notes

Reaction equation

HRID 1596211 reaction equation
[CH2:1]([NH:8][C:9]([CH:11]1[CH2:16][N:15]([N:17]=O)[CH2:14][CH2:13][N:12]1[C:19](=[O:21])[CH3:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O.C(O)(=O)C.[Zn]>[CH2:1]([NH:8][C:9]([CH:11]1[CH2:16][N:15]([NH2:17])[CH2:14][CH2:13][N:12]1[C:19](=[O:21])[CH3:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 21701706HCID 21701706, compound

Product 1

HCID 21701679HCID 21701679, compoundYield 43.9%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of rac-N-benzyl-1-acetyl-4-nitrosopiperazine-2-carboxamide (655 mg) in water (2 ml) and acetic acid (0.65 ml) was added zinc powder (443 mg) as portions during the period of 2 hours at 8-13° C. (exothermic reaction) with ice-water cooling bath. After removal of the bath, the temperature was raised till 55° C. and the reaction mixture was additionally stirred at 30-40° C. for 2 hours. The zinc residue was filtered off and washed with methanol (50 ml) on the Celite. The combined filtrate was added into dichloromethane (40 ml) and sodium hydroxide (460 mg) in water (6 ml) below 35° C. The resulting precipitate was filtered off with Celite and the residue was washed with chloroform (50 ml). The combined filtrate was washed with water, dried over magnesium sulfate and concentrated to give rac-N-benzyl-1-acetyl-4-aminopiperazine-2-carboxamide (274 mg). This product was used for next step without purification.

Workup

  1. custom(exothermic reaction) with ice-water cooling bath
  2. customAfter removal of the bath
  3. filtrationThe zinc residue was filtered off
  4. washwashed with methanol (50 ml) on the Celite
  5. additionThe combined filtrate was added into dichloromethane (40 ml) and sodium hydroxide (460 mg) in water (6 ml) below 35° C
  6. filtrationThe resulting precipitate was filtered off with Celite
  7. washthe residue was washed with chloroform (50 ml)
  8. washThe combined filtrate was washed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-cb4c723cc478469ea641375baeb5f40b
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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