Triethylamine → N-(4-((4-(pyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)propionamide

HRID 1282135Notes

Reaction equation

HRID 1282135 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:12][CH2:11]2)=[CH:5][CH:4]=1.[C:22](Cl)(=[O:25])[CH2:23][CH3:24].C(N(CC)CC)C>C(Cl)Cl>[N:21]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:13]1[CH2:12][CH2:11][N:10]([CH2:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][NH:1][C:22](=[O:25])[CH2:23][CH3:24])=[CH:4][CH:5]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 184230082-(4-(4-(Aminomethyl)phenylmethyl)piperazin-1-yl)pyrimidine

Product 1

HCID 18423155N-(4-((4-(pyrimidin-2-yl)piperazin-1-yl)methyl)phenylmethyl)propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-(4-(aminomethyl)phenylmethyl)piperazin-1-yl)pyrimidine (0.5 g), propionic chloride (0.18 ml) and triethylamine (0.3 ml) in methylene chloride (20 ml) was stirred at room temperature for 2 hr. The reaction mixture was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a pale-yellow substance (0.8 g). The obtained pale-yellow substance was crystallized from hexane/ethyl acetate (1:1, 50 ml) to give the title compound (0.5 g) as pale-yellow crystals.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customto give a pale-yellow substance (0.8 g)
  5. customThe obtained pale-yellow substance was crystallized from hexane/ethyl acetate (1:1, 50 ml)

Sources & evidence

ORD record
ord-6364f0b9980148818ad4fcac88e24980
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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