Methanol → 1-(4-{2-[5-(4-Acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)methanamine

HRID 1465478Notes

Reaction equation

HRID 1465478 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[N:12][C:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]=[N+]=[N-])=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CO>C(OCC)(=O)C.[C].[Pd]>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:24][NH2:25])=[CH:22][CH:23]=3)=[N:12][CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 581812991-Acetyl-4-(6-{2-[4-(azidomethyl)phenyl]ethyl}pyridin-3-yl)piperazine

Product 1

HCID 581813361-(4-{2-[5-(4-Acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)methanamineYield 68.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-acetyl-4-(6-{2-[4-(azidomethyl)phenyl]ethyl}pyridin-3-yl)piperazine (226.8 mg, 0.622 mmol) in ethyl acetate (10 ml) was added 10% palladium carbon (45.1 mg, 50% containing water), and the mixture was hydrogenated at room temperature, under atmospheric pressure. Methanol (10 ml) was added to the reaction mixture, and the reaction mixture was filtered through Celite. The filtrate was concentrated under reduced pressure, and the residue was washed with a mixture of ethyl acetate/diisopropyl ether (1:1) and dried under reduced pressure to give 1-(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)methanamine (144.0 mg, yield 68.2%) as a white solid.

Workup

  1. customwas hydrogenated at room temperature, under atmospheric pressure
  2. filtrationthe reaction mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washthe residue was washed with a mixture of ethyl acetate/diisopropyl ether (1:1)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f4c01234bacd49c8b54d5a1950ab11fd
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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