Formaldehyde → 2-(N-Benzylmethylamino)-methyl-cyclopentanone hydrochloride

HRID 1156514Notes

Reaction equation

HRID 1156514 reaction equation
[ClH:1].[CH2:2]([CH2:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:11]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12]1.[CH2:17]=O>C(O)C>[ClH:1].[CH2:2]([CH2:9][NH:10][C:12]1([CH3:17])[CH2:13][CH2:14][CH2:15][C:11]1=[O:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8452CyclopentanoneHCID 90752-Phenylethylamine hydrochloride

Product 1

HCID 205348202-(N-Benzylmethylamino)-methyl-cyclopentanone hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

87.5 g (0.55 mole) of N-benzylmethylamine hydrochloride, 84 g (1.0 mole) of cyclopentanone, 45 g of paraformaldehyde (1.5 moles of formaldehyde) and 500 ml of ethanol are refluxed for one hour whilst stirring, during which solution occurs. After the solution has cooled, the solvent is distilled off under reduced pressure, the oily residue is dissolved in 100 ml of isopropanol and 500 ml of ethyl acetate are then added, whereupon the product crystallizes out after some time.

Workup

  1. temperatureAfter the solution has cooled
  2. distillationthe solvent is distilled off under reduced pressure
  3. dissolutionthe oily residue is dissolved in 100 ml of isopropanol
  4. addition500 ml of ethyl acetate are then added, whereupon the product
  5. customcrystallizes out after some time

Sources & evidence

ORD record
ord-9d9414fdde024aa4b7fa304517744a99
Source dataset
uspto-grants-1982_06
Patent number
US04336263

Reaction notes

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