Formic Acid → HCID 13314310, compound

HRID 615313Notes

Reaction equation

HRID 615313 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]([OH:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C1C=CC=CC=1.C(O)=O.C=O>C(O)C>[CH3:1][NH:8][CH2:9][CH2:10][C:11]([OH:26])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:12][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 13314307HCID 13314307, compound

Product 1

HCID 13314310HCID 13314310, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

45 g (0.13 mole) of N-benzyl-3-hydroxy-3-phenyl-4-phenoxybutylamine prepared as described in (c) were dissolved in 400 ml of ethanol, and 7.8 g of formic acid and 20 g of 35% strength formaldehyde solution were added in succession at the boiling point. After 3 hours, the alcohol was distilled off, 200 ml of 2N sodium hydroxide solution were added to the residue and the mixture was extracted with 3 times 2 ml of ether. The solution was dried and then evaporated down, the residue was taken up in 250 ml of acetic acid and the solution was hydrogenated in a shaken flask, using 5 g of palladium on carbon as the catalyst. When absorption of hydrogen was complete, the mixture was filtered, the filtrate was evaporated down, 2N sodium hydroxide solution was added and the mixture was extracted with 3 times 200 ml of ether. After the solvent had been distilled off, the product solidified. 22 g (65%) of N-methyl-3-hydroxy-3-phenyl-4-phenoxybutylamine of melting point 98°-99° C. were obtained.

Workup

  1. distillationthe alcohol was distilled off
  2. addition200 ml of 2N sodium hydroxide solution were added to the residue
  3. extractionthe mixture was extracted with 3 times 2 ml of ether
  4. customThe solution was dried
  5. customevaporated down
  6. customthe solution was hydrogenated in a shaken flask
  7. customWhen absorption of hydrogen
  8. filtrationthe mixture was filtered
  9. customthe filtrate was evaporated down
  10. addition2N sodium hydroxide solution was added
  11. extractionthe mixture was extracted with 3 times 200 ml of ether
  12. distillationAfter the solvent had been distilled off

Sources & evidence

ORD record
ord-b9c9f6f771be4936a30c27fff82ebd9c
Source dataset
uspto-grants-1985_02
Patent number
US04499087

Reaction notes

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