Phenyl chloroformate → HCID 14151626, compound

HRID 364135Notes

Reaction equation

HRID 364135 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][N:12]3C.[Cl:18]C(OC1C=CC=CC=1)=O>C1(C)C=CC=CC=1>[ClH:18].[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

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 14151633HCID 14151633, compound

Product 1

HCID 14151626HCID 14151626, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 628 mg of trans-7-methoxy-4-methyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine and 1 g of phenyl chloroformate in 20 ml of toluene is refluxed for 3 hours. After dilution with ether and washing with aqueous hydrochloric acid, the solvent is removed and 1 g of potassium hydroxide and 20 ml of dioxane is added. After refluxing for 2 hours, the reaction is diluted with water and the product extracted with ether. After drying and removal of solvent, the hydrochloride salt is prepared from ethanolic hydrogen chloride to afford trans-7-methoxy-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride, m.p. 207°-210°.

Workup

  1. washAfter dilution with ether and washing with aqueous hydrochloric acid
  2. customthe solvent is removed
  3. addition1 g of potassium hydroxide and 20 ml of dioxane is added
  4. temperatureAfter refluxing for 2 hours
  5. additionthe reaction is diluted with water
  6. extractionthe product extracted with ether
  7. customAfter drying
  8. customremoval of solvent

Sources & evidence

ORD record
ord-7da58210796c4ec089d8f3533546c598
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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