Benzyl Chloride → HCID 13307202, compound

HRID 1903306Notes

Reaction equation

HRID 1903306 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:16]3[S:30][CH2:29][CH2:28][CH2:27][C:17]=3[N:18]=[C:19]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:20]=2)[CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([N:24]1[CH2:25][CH2:26][N:21]([C:19]2[N:20]=[C:15]([N:12]3[CH2:13][CH2:14][O:9][CH2:10][CH2:11]3)[C:16]3[S:30][CH2:29][CH2:28][CH2:27][C:17]=3[N:18]=2)[CH2:22][CH2:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 13307197HCID 13307197, compound

Product 1

HCID 13307202HCID 13307202, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.6 g of benzyl chloride was added dropwise to a mixture of 3 g of 4-morpholino-2-piperazino-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine, 4 g of potassium carbonate and 30 ml of N,N-dimethylformamide at room temperature under stirring, followed by stirring for 5 hours. The reaction solution was extracted with ethyl acetate, and the extract was washed with water and dried. The solvent was then distilled off and the resulting crystals were recrystallized from a mixture of diethyl ether-petroleum ether to obtain 3.1 g (82% yield) of 2-(N-benzylpiperazino)-4-morpholino-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine as pale yellow prisms having a melting point of 125° C.

Workup

  1. stirringby stirring for 5 hours
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. customdried
  5. distillationThe solvent was then distilled off
  6. customthe resulting crystals were recrystallized from a mixture of diethyl ether-petroleum ether

Sources & evidence

ORD record
ord-0a4b86e91e5c478d8e6a3fc0b43c6362
Source dataset
uspto-grants-1984_03
Patent number
US04435566

Reaction notes

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