N-Methyl-2-piperidone → 1-(3-Chlorophenyl)-3-(1-methyl-2-piperidylidene)-2(1H,3H)-indolone

HRID 1110863Notes

Reaction equation

HRID 1110863 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][C:9]2=[O:17])[CH:5]=[CH:6][CH:7]=1.[CH3:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]1=O>CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[C:20]3[CH2:21][CH2:22][CH2:23][CH2:24][N:19]3[CH3:18])[C:9]2=[O:17])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13603N-Methyl-2-piperidoneHCID 112995301-(3-Chlorophenyl)-indolin-2-one

Product 1

HCID 537324371-(3-Chlorophenyl)-3-(1-methyl-2-piperidylidene)-2(1H,3H)-indolone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

By the procedure of Example B1, but using 1:1 hexane:ethyl acetate as chromatography eluant and pentane for crystallization, 1-(3-chlorophenyl-2-(1H,3H)-indolone (2.0 g, 8.2 mmoles) and N-methyl-2-piperidone (1.3 ml, 11.5 mmoles) were converted to title product, 180 mg (6.5%) m.p. 162°-165°.

Workup

  1. customethyl acetate as chromatography eluant and pentane for crystallization

Sources & evidence

ORD record
ord-c8317a8f5cef47e98ac03d172d7d55c2
Source dataset
uspto-grants-1990_12
Patent number
US04977178

Reaction notes

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