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

HRID 918144Notes

Reaction equation

HRID 918144 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 30 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. Elementary analysis: C20H28N2OCl2.1/2H2O Calcd. C, 61.21; H, 7.45; N, 7.14 Found C, 60.91; H, 7.60; N, 7.25.

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-2eccda436fb44c31b2d6cb9ee051ae21
Source dataset
uspto-grants-1976_07
Patent number
US03969409

Reaction notes

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