HCID 20255643, compound → HCID 20255656, compound

HRID 637696Notes

Reaction equation

HRID 637696 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH3:17])[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:10][C:5]=2[O:4][CH:3]=1>[Pd].C(OCC)(=O)C>[CH3:1][CH:2]1[C:6]2[CH:7]=[C:8]([CH3:17])[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 1

HCID 20255643HCID 20255643, compound

Product 1

HCID 20255656HCID 20255656, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 10 g (43.2 mmole) of 3,5-dimethyl-6-morpholinobenzofuran, 2 g of 5% palladium on carbon and 200 ml of ethyl acetate is hydrogenated at room temperature and a pressure of 4 bar. For completion of the reaction, 2 g, each time, of 5% palladium on carbon are added a further four times during hydrogenation. After a total of 58 hours, the catalyst is filtered off and the filtrate is concentrated by evaporation in vacuo. Purification of the residue by flash chromatography (silica gel, petroleum ether/ether) and distillation of the pure fractions in a bulb tube (130°-140°/6.10-2 torr) yields 3,5-dimethyl-6-morpholino-2,3-dihydrobenzofuran having a melting point of 57°-58°.

Workup

  1. customis hydrogenated at room temperature
  2. customFor completion of the reaction, 2 g
  3. filtrationAfter a total of 58 hours, the catalyst is filtered off
  4. concentrationthe filtrate is concentrated by evaporation in vacuo
  5. customPurification of the residue
  6. distillationby flash chromatography (silica gel, petroleum ether/ether) and distillation of the pure fractions in a bulb tube (130°-140°/6.10-2 torr)

Sources & evidence

ORD record
ord-97a95d292f924d488d456a123b790900
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

Loading…