Formaldehyde → 2-Cyclohexen-1-one, 5,5-dimethyl-3-(2-chlorophenylamino)-2-piperidinomethyl-, monohydrochloride

HRID 461674Notes

Reaction equation

HRID 461674 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[NH:4][C:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[CH2:8][C:7](=[O:13])[CH:6]=1.[CH2:18]=O.Cl.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CO.C(O)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[NH:4][C:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[CH2:8][C:7](=[O:13])[C:6]=1[CH2:18][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 2723721Piperidine, hydrochloride (1:1)HCID 13002203HCID 13002203, compound

Product 1

HCID 30399422-Cyclohexen-1-one, 5,5-dimethyl-3-(2-chlorophenylamino)-2-piperidinomethyl-, monohydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

12.5 Parts of 3-(2-chloroanilino)-5,5-dimethyl-2-cyclohexen-1-one is dissolved in 3o volume parts of methanol under warming and, then, to the resulting solution are added 4.5 parts of a 37 weight % aqueous solution of formaldehyde, 6.05 parts of piperidine hydrochloride and 2 drops of glacial acetic acid. The whole mixture is allowed to stand at room temperature for 1 hour, whereupon a yellow, clear solution is obtained. The methanol is distilled off under reduced pressure, and a small amount of isopropyl ether is added to the resulting residue, followed by cooling, whereupon colorless crystals separate. The crystals are collected by filtration and recrystallized from acetone. The procedure yields colorless prisms of 3-(2-chloroanilino)-5,5-dimethyl-2-piperidinomethyl-2-cyclohexen-1-one hydrochloride. Melting point: 105°-106° C.

Workup

  1. temperatureunder warming
  2. customwhereupon a yellow, clear solution is obtained
  3. distillationThe methanol is distilled off under reduced pressure
  4. additiona small amount of isopropyl ether is added to the resulting residue
  5. temperatureby cooling, whereupon colorless crystals
  6. customseparate
  7. filtrationThe crystals are collected by filtration
  8. customrecrystallized from acetone

Sources & evidence

ORD record
ord-bb0aff482f9442e99eabb0b12a075675
Source dataset
uspto-grants-1977_12
Patent number
US04064133

Reaction notes

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