Sodium Hydroxide → 2-(4-(4-(Aminomethyl)phenylmethyl)piperazin-1-yl)pyrimidine

HRID 1282134Notes

Reaction equation

HRID 1282134 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH:21]C(=O)C)=[CH:16][CH:15]=2)[CH2:9][CH2:8]1.[OH-].[Na+]>Cl>[NH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]2[CH2:9][CH2:8][N:7]([C:2]3[N:1]=[CH:6][CH:5]=[CH:4][N:3]=3)[CH2:12][CH2:11]2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11702585N-(4-((4-(Pyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide

Product 1

HCID 184230082-(4-(4-(Aminomethyl)phenylmethyl)piperazin-1-yl)pyrimidineYield 63.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-(4-((4-(Pyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)acetamide (4.0 g) was dissolved in 10% hydrochloric acid (50 ml) and the solution was refluxed under heating for 12.5 hr. To the reaction mixture was added 10% aqueous sodium hydroxide solution to make it alkaline, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was crystallized from diisopropyl ether to give the title compound (2.2 g) as pale-yellow crystals, m.p.=70-72° C.

Workup

  1. temperaturethe solution was refluxed
  2. temperatureunder heating for 12.5 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-e710ec5cf84940cf8a881d0dfcf6e632
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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