Dimethylamine → HCID 12577736, compound

HRID 918142Notes

Reaction equation

HRID 918142 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. Elementary analysis: C17H24N2O Calcd. C, 74.95; H, 8.88; N, 10.28 Found C, 75.28; H, 8.96; N, 10.50.

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-d5d25b65e4a9489ca2e45e36debd3f07
Source dataset
uspto-grants-1976_07
Patent number
US03969409

Reaction notes

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