Allyl chloride → Hydrochloric Acid

HRID 364144Notes

Reaction equation

HRID 364144 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][C@@H:11]3[C@@H:16]([C:7]=2[CH:6]=[CH:5][CH:4]=1)[CH2:15][CH2:14][CH2:13][NH:12]3.[CH2:17]([Cl:20])[CH:18]=[CH2:19].C(=O)([O-])[O-].[Ca+2]>CN(C)C=O>[ClH:20].[ClH:20].[CH2:19]([N:12]1[CH2:13][CH2:14][CH2:15][C@@H:16]2[C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[O:9][CH2:10][C@@H:11]12)[CH:18]=[CH2:17]

Participants

6

Reactant 3

HCID 7850Allyl chlorideHCID 10112Calcium CarbonateHCID 14151627HCID 14151627, compound

Product 2

HCID 313Hydrochloric AcidHCID 86740948HCID 86740948, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.19 g of trans-7-methoxy-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine, 0.80 g of allyl chloride, 2.0 g of calcium carbonate in 20 ml of dry dimethylformamide is heated at 80° for 16 hours. After dilution with water the product is extracted with ether. After drying over magnesium sulfate the solvent is removed in vacuo. Acidification with ethanolic hydrochloric acid affords trans-4-allyl-7-methoxy-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride. Hydrogenation of said compound in the presence of 500 mg of 10% palladium on carbon catalyst at 3 atm. pressure for 6 hours at room temperature in water affords trans-7-methoxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride.

Workup

  1. temperatureis heated at 80° for 16 hours
  2. extractionAfter dilution with water the product is extracted with ether
  3. dry with materialAfter drying over magnesium sulfate the solvent
  4. customis removed in vacuo

Sources & evidence

ORD record
ord-4d2f077449e04dc2a68cd53c6d0f675a
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

Loading…