Sodium Chloride → HCID 54317729, compound

HRID 1462522Notes

Reaction equation

HRID 1462522 reaction equation
Cl[CH2:2][CH:3]=[CH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2.[CH2:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[Na+].C(=O)([O-])O.[Na+]>CN(C)C=O.C(N(CC)CC)C>[CH2:16]([N:23]1[CH2:28][CH2:27][N:26]([CH2:2][CH:3]=[CH:4][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]3)[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 759941-BenzylpiperazineHCID 516892Sodium BicarbonateHCID 54570479HCID 54570479, compound

Product 1

HCID 54317729HCID 54317729, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

2.3 Grams of 6-(3-chloro-1-propenyl)-3,4-dihydrocarbostyril, 2.0 g of 4-benzylpiperazine and 2.0 ml of triethylamine were mixed in 50 ml of dimethylformamide and the mixture was stirred at 50° C. for 3 hours. The reaction mixture was poured into a mixture of 50 ml of a saturated sodium chloride aqueous solution with 50 ml of 5% of sodium hydrogencarbonate aqueous solution, and the organic layer was extracted with chloroform. The chloroform layer was washed with water and dried, then chloroform was removed by distillation to obtain a residue. The residue was recrystallized from ethanol-water to obtain 2.1 g of 6-[3-(4-benzylpiperazinyl)-1-propenyl]-3,4-dihydrocarbostyril, having the melting point of 151°-153° C. in colorless needle-like crystals. Then 2.1 g of 6-[3-(4-benzylpiperazinyl)-1-propenyl]-3,4-dihydrocarboxtyril, 0.2 g of platinum black and 2 ml of concentrated hydrochloric acid were mixed with 100 ml of ethanol and the mixture was subjected to catalytic reduction under 3 kg/cm2 of hydrogen gas at a room temperature for 5 hours. The reaction mixture was filtered and the mother liquor was concentrated to obtain a residue. The residue was recrystallized from methanol to obtain 1.8 g of 6-(3-piperzinopropyl)-3,4-dihydrocarbostyril dihydrochloride in colorless needle-like crystals. Melting point: 275° -278° C. (decomposed).

Workup

  1. extractionthe organic layer was extracted with chloroform
  2. washThe chloroform layer was washed with water
  3. customdried
  4. customchloroform was removed by distillation
  5. customto obtain a residue
  6. customThe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-fab3283114124decb68171e513b36dfb
Source dataset
uspto-grants-1984_07
Patent number
US04460593

Reaction notes

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