Hydrochloric Acid → 5-(Dimethylamino)-1-phenylpent-1-en-3-one

HRID 435113Notes

Reaction equation

HRID 435113 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.[CH2:12]=O.Cl.[CH3:15][NH:16][CH3:17]>>[CH3:15][N:16]([CH3:12])[CH2:17][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 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 159094-Phenyl-3-Buten-2-one

Product 1

HCID 1457905-(Dimethylamino)-1-phenylpent-1-en-3-one

Procedure

Analogously to Examples 1 and 2, 4-phenyl-3-butene-2-one is reacted with paraformaldehyde, HCl and dimethylamine to produce 5-dimethylamino-1-phenyl-1-penten-3-one. 2.2 g of this amine and 16.1 g of methyl iodide are combined in 40 ml of diethyl ether and the mixture is stirred. After 10 minutes a white precipitate forms, and after 30 minutes, 50 ml of diethyl ether is added to maintain a stirrable slurry. The precipatate is filtered, washed with diethyl ether and dried in a dessicator to produce E-N,N,N-trimethyl-3-ox-5-phenyl-4-penten-1-aminium iodide, m.p. 204°-206° C.

Sources & evidence

ORD record
ord-73d069adbdd84d1d9864b8f2feb7482e
Source dataset
uspto-grants-1983_08
Patent number
US04400380

Reaction notes

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