Formaldehyde → HCID 12577737, compound

HRID 461673Notes

Reaction equation

HRID 461673 reaction equation
[NH:1]([C:8]1[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:10](=[O:16])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]=O.[ClH:19].[CH3:20][NH:21][CH3:22]>CO.C(O)(=O)C>[ClH:19].[NH:1]([C:8]1[CH2:13][C:12]([CH3:14])([CH3:15])[CH2:11][C:10](=[O:16])[C:9]=1[CH2:20][N:21]([CH3:17])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 2058962-Cyclohexen-1-one, 5,5-dimethyl-3-(phenylamino)-

Product 1

HCID 12577737HCID 12577737, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

2.15 Parts of 3-anilino-5,5-dimethyl-2-cyclohexen-1-one is dissolved in 10 volume parts of methanol under warming and, then, to the resulting solution 0.9 part of a 37 weight % aqueous solution of formaldehyde, 0.81 part of dimethylamine hydrochloride and 1 drop of glacial acetic acid are added. The whole mixture is allowed to stand at room temperature for 1 hour, and after which time, the methanol is distilled off under reduced pressure. To the resulting residue is added, a small amount of isopropyl ether, followed by cooling, whereupon colorless crystals separate. The crystals are collected by filtration and recrystallized from acetone. The procedure yields colorless needles of 3-anilino-5,5-dimethyl-2-dimethylaminomethyl-2-cyclohexen-1-one hydrochloride. Melting point: 169°-170° C

Workup

  1. temperatureunder warming
  2. distillationafter which time, the methanol is distilled off under reduced pressure
  3. additionTo the resulting residue is added
  4. temperatureby cooling, whereupon colorless crystals
  5. customseparate
  6. filtrationThe crystals are collected by filtration
  7. customrecrystallized from acetone

Sources & evidence

ORD record
ord-b3d53ead68834760893b835523ee1225
Source dataset
uspto-grants-1977_12
Patent number
US04064133

Reaction notes

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