Hydrochloric Acid → 6-(4-Geranyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril hydrochloride

HRID 231108Notes

Reaction equation

HRID 231108 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([OH:3])=O.S(Cl)([Cl:17])=O.[CH2:19]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)/[CH:20]=[C:21](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])\[CH3:22].Cl.C(O)C.Cl>C(Cl)Cl.N1C=CC=CC=1>[ClH:17].[CH2:19]([N:29]1[CH2:30][CH2:31][N:32]([C:1]([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]3)=[O:3])[CH2:33][CH2:34]1)/[CH:20]=[C:21](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:27])[CH3:28])\[CH3:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 71319092-Oxo-1,2,3,4-tetrahydroquinoline-6-carboxylic acidHCID 14497703GeranylpiperazineHCID 21887872Ethanol hydrochloride

Product 1

HCID 200345276-(4-Geranyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril hydrochloride

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.9 Grams of 6-carboxy-3,4-dihydrocarbostyril was suspended in 200 ml of methylene chloride, then 2 ml of pyridine was added thereto. The mixture was kept at 0°-20° C., under stirring condition, 1.4 g of thionyl chloride was added dropwise. After the dropwise addition was finished, the whole reaction mixture was stirred for 1 hour at the same temperature, and 10 ml of methylene chloride containing 2.19 g of geranylpiperazine was added dropwise. After the dropwise addition was finished, the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was thoroughly washed with an aqueous solution of potassium carbonate, then further washed with water and diluted hydrochloric acid, then dried with anhydrous sodium sulfate, and the solvent was removed by evaporation. The residue thus obtained was converted into hydrochloride by adding ethanol-hydrochloric acid, and recrystallized from ethanol-water to obtain 343 mg of 6-(4-geranyl-1-piperazinylcarbonyl)-3,4-dihydrocarbostyril hydrochloride.monohydrate. Colorless needle-like crystals. Melting point: 265°-266° C. (dec.).

Workup

  1. customwas kept at 0°-20° C.
  2. additionwas added dropwise
  3. additionAfter the dropwise addition
  4. customthe whole reaction mixture
  5. additionwas added dropwise
  6. additionAfter the dropwise addition
  7. washThe reaction mixture was thoroughly washed with an aqueous solution of potassium carbonate
  8. washfurther washed with water and diluted hydrochloric acid
  9. dry with materialdried with anhydrous sodium sulfate
  10. customthe solvent was removed by evaporation
  11. customThe residue thus obtained
  12. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-884a19504fd44abb974f542c6f4369de
Source dataset
uspto-grants-1989_07
Patent number
US04845100

Reaction notes

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