Allyl chloride → HCID 70536330, compound

HRID 1649236Notes

Reaction equation

HRID 1649236 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH2:16][CH2:17][C:18](=[O:24])[NH:19]3)[CH2:10][CH2:9]1)=[O:7].[NH2-].[Na+].[CH2:32](Cl)[CH:33]=[CH2:34]>CN(C=O)C>[OH2:2].[CH2:34]([N:19]1[C:20]2[C:15](=[C:14]([N:11]3[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]4[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:9][CH2:10]3)[CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:17][C:18]1=[O:24])[CH:33]=[CH2:32].[CH2:34]([N:19]1[C:20]2[C:15](=[C:14]([N:11]3[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]4[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:9][CH2:10]3)[CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:17][C:18]1=[O:24])[CH:33]=[CH2:32]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 24533Sodium amideHCID 13236333HCID 13236333, compound

Product 1

HCID 70536330HCID 70536330, compoundYield 119.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[4-(3,4-Dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (1.96 g) and 0.20 g of sodium amide were mixed with 60 ml of DMF and stirred at room temperature for 2 hours. Then, to the mixture was added 0.67 g of allyl chloride and the mixture was stirred at room temperature for 10 hours. The reaction mixture was poured into 150 ml of saturated saline solution and organic substances were extracted with chloroform. The chloroform layer was washed with water and dehydrated. Chloroform was distilled off and the residue was purified through silica gel column chromatography followed by recrystallization from methanol-ether to give 1.76 g of 1-allyl-5-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril hemihydrate, m.p. 120°-122° C., colorless granules.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 hours
  2. extractionwere extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. distillationChloroform was distilled off
  5. customthe residue was purified through silica gel column chromatography
  6. customfollowed by recrystallization from methanol-ether

Sources & evidence

ORD record
ord-f328352f54984c88baa18bac7314dec4
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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