Formaldehyde → HCID 20531688, compound

HRID 1759319Notes

Reaction equation

HRID 1759319 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][NH:6][CH2:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[OH:9].[CH2:24]=O>C(O)=O>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][N:6]([CH3:24])[CH2:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[OH:9]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 20531701HCID 20531701, compound

Product 1

HCID 20531688HCID 20531688, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 1.85 g. (0.0058 m) of N-(2-methoxybenzyl)-1-(3,4-dimethoxyphenyl)-2-aminoethanol prepared as in Example 3, 4.8 ml of 90% formic acid and 4.5 ml of 37% formaldehyde was heated in a steam bath for 18 hours. The aqueous portion was evaporated and the residue redissolved in water. After making the solution acid with concentrated hydrochloroic acid, the mixture was heated for 20 minutes, cooled, made basic and extracted with chloroform. The organic extract was washed with water, brine then dried. Evaporation gave 1.8 g (93%) of N-(2-methoxybenzyl)-1-(3,4-dimethoxyphenyl)-N-methyl-2-amino ethanol as an oil.

Workup

  1. additionA mixture of 1.85 g
  2. temperaturewas heated in a steam bath for 18 hours
  3. customThe aqueous portion was evaporated
  4. dissolutionthe residue redissolved in water
  5. concentrationwith concentrated hydrochloroic acid
  6. temperaturethe mixture was heated for 20 minutes
  7. temperaturecooled
  8. extractionextracted with chloroform
  9. extractionThe organic extract
  10. washwas washed with water, brine
  11. customthen dried
  12. customEvaporation

Sources & evidence

ORD record
ord-17e0ed5a363248feaa1889abfa120db1
Source dataset
uspto-grants-1982_07
Patent number
US04340600

Reaction notes

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