HCID 21701702, compound → HCID 21701694, compound

HRID 1596210Notes

Reaction equation

HRID 1596210 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][N:14]([N:18]=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O.C(O)(=O)C.[Zn]>[NH2:18][N:14]1[CH2:15][CH2:16][CH2:17][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12][CH2:13]1

Participants

5

Reactant 1

HCID 21701702HCID 21701702, compound

Product 1

HCID 21701694HCID 21701694, compoundYield 72.9%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of 1-benzyloxycarbonyl-4-nitrosohomopiperazine (1.0 g) in water (2.0 ml) and acetic acid (1.09 ml) was added zinc powder (745 mg) 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 1 hour. Acetic acid (1.09 ml) and zinc powder (745 mg) was added to the reaction mixture and stirred at 40° for 1 hour. After cooling, zinc residue was filtered off and washed with methanol (5 ml) on the Celite. The combined filtrate was added into dichloromethane (10 ml) and sodium hydroxide (1.6 g) in water (5 ml) below 35° C. The resulting precipitate was filtered off with Celite and the residue was washed with dichloromethane (20 ml). The combined filtrate was dried over magnesium sulfate and filtered. The filtrate was condensed in vacuo to give 1-amino-4-benzyloxycarbonylhomopiperazine (690 mg). This product was used for next step without further purification.

Workup

  1. custom(exothermic reaction) with ice-water cooling bath
  2. customAfter removal of the bath
  3. additionAcetic acid (1.09 ml) and zinc powder (745 mg) was added to the reaction mixture
  4. stirringstirred at 40° for 1 hour
  5. temperatureAfter cooling
  6. filtrationzinc residue was filtered off
  7. washwashed with methanol (5 ml) on the Celite
  8. additionThe combined filtrate was added into dichloromethane (10 ml) and sodium hydroxide (1.6 g) in water (5 ml) below 35° C
  9. filtrationThe resulting precipitate was filtered off with Celite
  10. washthe residue was washed with dichloromethane (20 ml)
  11. dry with materialThe combined filtrate was dried over magnesium sulfate
  12. filtrationfiltered
  13. customcondensed in vacuo

Sources & evidence

ORD record
ord-97dbe4cbd4c949ad95f44c4e7a1a9b89
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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