Isopropyl Acetate → 3-(Dimethylamino)-2-(4-fluorophenyl)-1-phenylprop-2-en-1-one

HRID 1608285Notes

Reaction equation

HRID 1608285 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.C(OC(C)C)(=O)C.CO[CH:26](OC)[N:27]([CH3:29])[CH3:28]>>[CH3:26][N:27]([CH3:29])[CH:28]=[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:9]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:10]

Participants

4

Reactant 3

HCID 7915Isopropyl AcetateHCID 78373Dimethylformamide dimethyl acetalHCID 2363292-(4-fluorophenyl)-1-phenylethanone

Product 1

HCID 545713423-(Dimethylamino)-2-(4-fluorophenyl)-1-phenylprop-2-en-1-one

Procedure

Following the procedure of example 1B, 13.8 g (0.0645 mol) of 2-(4-fluorophenyl)-1-phenylethanone was reacted with 20 mL of dimethyl formamide dimethyl acetal to yield 13.6 g of 3-(dimethylamino)-2-(4-fluorophenyl)-1-phenyl-2-propen-1-one, mp 115°-116° from isopropyl acetate. The enamine (10.5 g, 0.039 mol) was reacted with 6.03 g (0.039 mol) of ethyl hydrazinoacetate hydrochloride to yield 12.1 g of product mp 86°-87° C. from methyl-t-butyl ether.

Sources & evidence

ORD record
ord-13b40588bda540d387306729b73b2f16
Source dataset
uspto-grants-1989_09
Patent number
US04870095

Reaction notes

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