Hydrochloric Acid → 1-[1-(4-Pyridyl)-4-piperidinylamino]-2-piperazinone trihydrochloride

HRID 2086235Notes

Reaction equation

HRID 2086235 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)[C:13](=[O:30])[CH2:12]1)=O)C1C=CC=CC=1.[ClH:31]>C(OCC)(=O)C.CO.[Pd]>[ClH:31].[ClH:31].[ClH:31].[N:27]1[CH:28]=[CH:29][C:24]([N:21]2[CH2:20][CH2:19][CH:18]([NH:17][N:14]3[CH2:15][CH2:16][NH:11][CH2:12][C:13]3=[O:30])[CH2:23][CH2:22]2)=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 178254544-Benzyloxycarbonyl-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone

Product 1

HCID 695456121-[1-(4-Pyridyl)-4-piperidinylamino]-2-piperazinone trihydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-benzyloxycarbonyl-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone (25.29 g) and an a 4N solution of hydrochloric acid in ethyl acetate (15.5 ml) in methanol (300 ml) was combined with 10% Pd/C (50% hydrated, 5.00 g) and stirred at room temperature for 15 hours under a hydrogen atmosphere. The catalyst was filtered off, and the reaction mixture was concentrated. The residue was dissolved in ethanol (300 ml), and combined with a 4N solution of hydrochloric acid in ethyl acetate (31 ml). The crystals precipitated were collected by filtration and dried to obtain 1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone trihydrochloride (20.16 g) as colorless crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in ethanol (300 ml)
  4. customThe crystals precipitated
  5. filtrationwere collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-0d55b9eb262941a982003bef791d5c1f
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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