Formaldehyde → HCID 21824593, compound

HRID 462107Notes

Reaction equation

HRID 462107 reaction equation
[CH2:1]1[O:14][C:13]2[C:3](=[CH:4][C:5]3[CH2:11][CH2:10][NH:9][CH2:8][CH2:7][C:6]=3[CH:12]=2)[O:2]1.[CH2:15]=O>CO>[CH3:15][N:9]1[CH2:10][CH2:11][C:5]2[CH:4]=[C:3]3[O:2][CH2:1][O:14][C:13]3=[CH:12][C:6]=2[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 21824590HCID 21824590, compound

Product 1

HCID 21824593HCID 21824593, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

19.1 g (0.1 M) of 2,3,4,5-tetrahydro-7,8-methylenedioxy-1H-3-benzazepine base was dissolved in 100 ml of methanol and 12 ml of 37% formaldehyde (0.148 moles) added thereto. In a few minutes, a new precipitate began to form with the evolution of heat. To this suspension 5 g of methanol-washed Raney nickel was added and the mixture shaken under 50 lbs. of hydrogen pressure. Uptake of hydrogen was complete in about an hour after which the excess hydrogen was vented, the catalyst removed by filtration, washed and the combined filtrates freed of solvent in the rotary evaporator. To remove the excess formaldehyde, the residue was dissolved in 100 ml of benzene, the solution washed four times with water, then dried, and the solvent distilled leaving a syrup. This was distilled from a small Claisen flask at reduced pressure, to yield three fractions. The fraction showing a boiling point of 166°-167°/mm contained the above-named product.

Workup

  1. waitIn a few minutes
  2. customto form with the evolution
  3. temperatureof heat
  4. washTo this suspension 5 g of methanol-washed Raney nickel
  5. additionwas added
  6. waitUptake of hydrogen was complete in about an hour
  7. customthe catalyst removed by filtration
  8. washwashed
  9. customthe combined filtrates freed of solvent in the rotary evaporator
  10. customTo remove the excess formaldehyde
  11. dissolutionthe residue was dissolved in 100 ml of benzene
  12. washthe solution washed four times with water
  13. customdried
  14. distillationthe solvent distilled
  15. customleaving a syrup
  16. distillationThis was distilled from a small Claisen flask at reduced pressure
  17. customto yield three fractions

Sources & evidence

ORD record
ord-92351bea4c94443bb29a91e9b29bcbad
Source dataset
uspto-grants-1977_12
Patent number
US04065473

Reaction notes

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