Formaldehyde → (E)-5-Dimethylamino-1-phenyl-pent-1-en-3-one; hydrochloride

HRID 46491Notes

Reaction equation

HRID 46491 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9](=[O:11])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:12].[CH3:13][NH:14][CH3:15].[CH2:16]=O>C(O)C>[ClH:12].[CH3:13][N:14]([CH3:16])[CH2:15][CH2:10][C:9](=[O:11])[CH:8]=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 637759Benzylideneacetone

Product 1

HCID 145789(E)-5-Dimethylamino-1-phenyl-pent-1-en-3-one; hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

trans-4-Phenyl-3-buten-2-one (14.6 g, 0.1 mole), dimethylamine hydrochloride (9.0 g, 0.1 mole) and paraformaldehyde (5.8 g, 0.2 mole) are heated at reflux in 150 ml of absolute ethanol for 3 hours. The reaction mixture is concentrated in vacuo, then washed with ether. Addition of ethyl acetate causes crystallization. The product is recrystallized from acetonitrile to yield 6.9 g, m.p. 150°-154° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. washwashed with ether
  3. additionAddition of ethyl acetate
  4. customcrystallization
  5. customThe product is recrystallized from acetonitrile
  6. customto yield 6.9 g, m.p. 150°-154° C.

Sources & evidence

ORD record
ord-f3e5da1636a14bf7a4e253b7767463fe
Source dataset
uspto-grants-1979_11
Patent number
US04173649

Reaction notes

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