4,6-Dichloropyrimidine → 4-(4-Benzylpiperazin-1-yl)-6-chloropyrimidine

HRID 2289528Notes

Reaction equation

HRID 2289528 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH2:9]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C>CC1C=CC(C)=CC=1>[CH2:9]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[N:3]=[CH:4][N:5]=[C:6]([Cl:8])[CH:7]=2)[CH2:18][CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 759941-BenzylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 186980524-(4-Benzylpiperazin-1-yl)-6-chloropyrimidine

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Conditions

Temperature
138 °C

Procedure

A mixture of 4,6-dichioropyrimidine (29.5 g), N-benzylpiperazine (44.0 g) and DIPEA (44 ml) was suspended in p-xylene (400 ml) and heated at 138° C. under reflux. After 18 hours the reaction mixture was allowed to cool to room temperature and filtered. The filtrate was evaporated using high vacuum pump apparatus to obtain 1-(benzyl)-4-(4-chloropyrimidin-6-yl)piperazine a brown solid, 60.5 g (105% based on 4,6-dichloropyrimidine);

Workup

  1. temperatureunder reflux
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a3c3fab9069f4f7b885d5509c7bd11f2
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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