Dichloromethane → HCID 68122726, compound

HRID 1730087Notes

Reaction equation

HRID 1730087 reaction equation
Br[CH2:2][C:3]([C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7][CH:6]=1)=[O:4].[N:16]1([CH2:22][CH2:23][CH2:24][NH2:25])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)[Cl:33]>>[ClH:33].[N:16]1([CH2:22][CH2:23][CH2:24][NH:25][CH:6]=[C:5]2[C:14](=[O:15])[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[O:7][CH2:2][C:3]2=[O:4])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 19049Piperidine-1-propylamineHCID 214864043-(Bromoacetyl)-4H-1-benzopyran-4-one

Product 1

HCID 68122726HCID 68122726, compound

Procedure

A mixture of 8.0g (0.03 mole) of 3-(bromoacetyl)chromone, 4.54g (0.032 mole) of piperidinopropylamine, 20g powdered potassium carbonate and 200ml of methylene chloride was stirred vigorously at room temperature for one hour. The red mixture was filtered, and the filtrate was washed well with water to remove the unreacted diamine. The organic phase was dried (K2CO3) and concentrated. The residue was taken-up into ether, and the solution was treated with excess hydrogen chloride to precipitate the crude hydrochloride salt. The ether was decanted, and the residue was dissolved in 100ml of warm 2-propanol. Upon addition of ether, crystals separated; wt. 3.8g (35%) of hygroscopic salt; m.p. 157°-159°. Recrystallization from ethanol-ether gave pure product; m.p. 158°-160°.

Workup

  1. filtrationThe red mixture was filtered
  2. washthe filtrate was washed well with water
  3. customto remove the unreacted diamine
  4. dry with materialThe organic phase was dried (K2CO3)
  5. concentrationconcentrated
  6. additionthe solution was treated with excess hydrogen chloride
  7. customto precipitate the crude hydrochloride salt
  8. customThe ether was decanted
  9. dissolutionthe residue was dissolved in 100ml of warm 2-propanol
  10. additionUpon addition of ether, crystals
  11. customseparated
  12. customRecrystallization from ethanol-ether
  13. customgave pure product

Sources & evidence

ORD record
ord-67f8ffa55af3469e96c0ea3a4fdb4f76
Source dataset
uspto-grants-1976_11
Patent number
US03991082

Reaction notes

Loading…