Cyproheptadine → HCID 20229455, compound

HRID 1285421Notes

Reaction equation

HRID 1285421 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12](=[O:16])[CH2:13][CH2:14][Cl:15])[NH:8][C:7](=[O:17])[CH2:6][CH2:5]2.[CH3:18][S:19](Cl)(=[O:21])=[O:20].CN1CCC(=C2C3C(=CC=CC=3)C=CC3C2=CC=CC=3)CC1.[Cl-].[Na+]>CN(C)C=O.N1C=CC=CC=1>[CH3:18][S:19]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12](=[O:16])[CH2:13][CH2:14][Cl:15])[NH:8][C:7](=[O:17])[CH2:6][CH2:5]2)(=[O:21])=[O:20]

Participants

7

Reactant 4

HCID 2913CyproheptadineHCID 5234Sodium ChlorideHCID 31297Methanesulfonyl chlorideHCID 13120785HCID 13120785, compound

Product 1

HCID 20229455HCID 20229455, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

5.06 Grams of 6-hydroxy-7-(3-chloropropionyl)-3,4-dihydrocarbostyril and 1.8 g of anhydrous pyridine were mixed with 50 ml of dimethylformamide. Then the mixture was cooled with ice and 2.5 g of methanesulfonyl chloride was added to the mixture and stirred at a room temperature for 3 hours. The reactin mixture was poured into 100 ml of a saturated sodium chloride solution and extracted with chloroform. The chloroform layer was washed with water, dried and chloroform was removed by distillation under a reduced pressure to obtain a residue. The residue was crystallized by adding 80 ml of hexane to obtain crude crystals. The crude materials were collected by filtration and were recrystallized from ethanol to obtain 4.5 g of 6-methylsulfonyloxy-7-(3-chloropropionyl)-3,4-dihydrocarbostyril in white crystals.

Workup

  1. additionwas added to the mixture
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. customdried
  5. customchloroform was removed by distillation under a reduced pressure
  6. customto obtain a residue
  7. customThe residue was crystallized
  8. additionby adding 80 ml of hexane
  9. customto obtain crude crystals
  10. filtrationThe crude materials were collected by filtration
  11. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-52c22e1f39514b27b885cbf7a804699e
Source dataset
uspto-grants-1986_01
Patent number
US04567187

Reaction notes

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