Formaldehyde → HCID 12577737, compound

HRID 918143Notes

Reaction equation

HRID 918143 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 recrystallizd 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 Elementary analysis: C17H25N2OC l Calcd. C, 66.10; H, 8.15; N, 9.07 Found C, 66.09; H, 8.21; N, 8.97.

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 and recrystallizd from acetone

Sources & evidence

ORD record
ord-ef77b0aa120b4d75969f2b47440dee62
Source dataset
uspto-grants-1976_07
Patent number
US03969409

Reaction notes

Loading…