N-methyl-2-pyrrolidone → HCID 86740936, compound

HRID 364134Notes

Reaction equation

HRID 364134 reaction equation
[ClH:1].C([O:5][C:6]1[C:11]2[O:12][CH2:13][C@@H:14]3[C@@H:19]([C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH2:18][CH2:17][CH2:16][N:15]3[CH3:20])C=C.CN1C[CH2:25][CH2:24][C:23]1=O>>[ClH:1].[OH:5][C:6]1[C:11]2[O:12][CH2:13][C@@H:14]3[C@@H:19]([C:10]=2[C:9]([CH2:23][CH2:24][CH3:25])=[CH:8][CH:7]=1)[CH2:18][CH2:17][CH2:16][N:15]3[CH3:20]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 86740938HCID 86740938, compound

Product 1

HCID 86740936HCID 86740936, compound

Procedure

A solution of 400 mg of trans-7-allyloxy-4-methyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride in 10 ml of 1-methyl-2-pyrrolidinone is heated for 2 hours at 190°, poured onto water and the products extracted with ethyl acetate. After drying over magnesium sulfate, the solvent is removed; the residue is 20 ml of ethanol is hydrogenated at 3 atm. pressure in the presence of 100 mg of 10% palladium on carbon catalyst for 3 hours. After filtration, the solvent is removed and the hydrochloride salt is prepared with ethanolic hydrogen chloride to afford trans-7-hydroxy-4-methyl-10-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride, m.p. 283°-285°.

Workup

  1. additionpoured onto water
  2. extractionthe products extracted with ethyl acetate
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent is removed
  5. filtrationAfter filtration
  6. customthe solvent is removed

Sources & evidence

ORD record
ord-6ce426a87e824329a2667a743d93a31f
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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