Formaldehyde → 2-[(Benzylmethylamino)methyl]cyclohexanone

HRID 131524Notes

Reaction equation

HRID 131524 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]=O.Cl.[CH2:11]([CH2:18][NH2:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)(=O)C>[CH2:11]([CH2:18][NH:19][CH2:8][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:1]1=[O:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 7967CyclohexanoneHCID 90752-Phenylethylamine hydrochloride

Product 1

HCID 205348122-[(Benzylmethylamino)methyl]cyclohexanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

37.6 ml cyclohexanone, 5.75 g paraformaldehyde, 38 ml glacial acetic acid and 30.2 g benzylmethylamine hydrochloride were heated at 105° C. (bath temperature) for 25 minutes, while stirring, the mixture was concentrated in vacuo (10 mbar), the residue was taken up in 100 ml 2-butanone and the mixture was concentrated again in vacuo. The residue was heated under reflux with 150 ml 2-butanone. After cooling to room temperature, the mixture was filtered and the residue on the filter was dried in vacuo. 36 g 2-[(benzylmethylamino)methyl]cyclohexanone were obtained.

Workup

  1. concentrationthe mixture was concentrated in vacuo (10 mbar)
  2. concentrationthe mixture was concentrated again in vacuo
  3. temperatureThe residue was heated
  4. temperatureunder reflux with 150 ml 2-butanone
  5. filtrationthe mixture was filtered
  6. customthe residue on the filter was dried in vacuo

Sources & evidence

ORD record
ord-4aab321dceac45439fbf90648b6f93fa
Source dataset
uspto-grants-2008_06
Patent number
US07384961B2

Reaction notes

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