Formaldehyde → HCID 15131078, compound

HRID 542176Notes

Reaction equation

HRID 542176 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[CH2:5][C@H:6]1[NH:11][CH2:10][CH2:9][O:8][C@@H:7]1[CH2:12]2.[CH2:17]=O.[H][H]>[Pd].CO>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[CH2:5][C@H:6]1[N:11]([CH3:17])[CH2:10][CH2:9][O:8][C@@H:7]1[CH2:12]2

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 15131076HCID 15131076, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15131078HCID 15131078, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

2 g of palladium on charcoal (10%) are suspended in 100 ml of methanol. To this are added 4.82 g (0.022M) of trans-3,4,4a,5,10,10a-hexahydro-6-methoxy-2H-naphth[2,3-b]-1,4-oxazine and 23.65 ml of formalin (37%), both dissolved in a total of 200 ml of methanol. The mixture is subsequently hydrogenated at 20°, at 1.2 bar hydrogen pressure. After 6 hours, the reaction mixture is filtered through a Hyflo suction filter, washed with 100 ml of methylene chloride, and the filtrate is concentrated by evaporation. The residue is taken up again in 100 ml of methylene chloride, and washed once each time with 20 ml of saturated potassium carbonate solution and water. The methylene chloride phase is dried and concentrated by evaporation. Trans-3,4,4a,5,10,10a-hexahydro-6-methoxy-4-methyl-2H-naphth[2,3-b]-1,4-oxazine is obtained (m.p. 268°-270°, recrystallisation from methylene chloride, methanol, acetone).

Workup

  1. filtrationthe reaction mixture is filtered through a Hyflo suction
  2. filtrationfilter
  3. washwashed with 100 ml of methylene chloride
  4. concentrationthe filtrate is concentrated by evaporation
  5. washwashed once each time with 20 ml of saturated potassium carbonate solution and water
  6. dry with materialThe methylene chloride phase is dried
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c6d0becfb2b949e3abb913068b8c8440
Source dataset
uspto-grants-1987_04
Patent number
US04656167

Reaction notes

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