Dimethylamine → HCID 12577736, compound

HRID 461672Notes

Reaction equation

HRID 461672 reaction equation
[CH2:1]=O.[CH3:3][NH:4][CH3:5].[NH:6]([C:13]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15](=[O:21])[CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CO.C(O)(=O)C>[NH:6]([C:13]1[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][C:15](=[O:21])[C:14]=1[CH2:3][N:4]([CH3:1])[CH3:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 2058962-Cyclohexen-1-one, 5,5-dimethyl-3-(phenylamino)-

Product 1

HCID 12577736HCID 12577736, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

In 10 volume parts of methanol is dissolved 2.15 parts of 3-anilino-5,5-dimethyl-2-cyclohexen-1-one under warming and, then, to the resulting solution 0.9 part of a 37 weight % aqueous solution of formaldehyde, 1.12 part of a 40 weight % aqueous solution of dimethylamine and 1 drop of glacial acetic acid are added. The whole mixture is allowed to stand at room temperature for 1 hour, after which time the methanol is distilled off under reduced pressure. A small amount of isopropanol is added to the resulting residue and the whole mixture is cooled, whereupon colorless crystals separate. The crystals are collected by filtration and recrystallized from isopropyl ether to obtain colorless prisms of 3-anilino-5,5-dimethyl-2-dimethylaminomethyl-2-cyclohexen-1-one. Melting point: 111°-112° C.

Workup

  1. temperatureunder warming
  2. distillationafter which time the methanol is distilled off under reduced pressure
  3. additionA small amount of isopropanol is added to the resulting residue
  4. temperaturethe whole mixture is cooled, whereupon colorless crystals
  5. customseparate
  6. filtrationThe crystals are collected by filtration
  7. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-9effb658ded04654a0c523b6d12dbda2
Source dataset
uspto-grants-1977_12
Patent number
US04064133

Reaction notes

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