4-Chloro-6-methoxyquinoline → 4-[3-(1-Acetyl-4-piperidyl)-1-propenyl]-6-methoxyquinoline

HRID 1729636

Reaction equation

HRID 1729636 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:14]([Li])CCC.[C:19]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH:29]=O)[CH2:24][CH2:23]1)(=[O:21])[CH3:20]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:19]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH:29]=[CH:14][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH2:24][CH2:23]1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 2283484-Chloro-6-methoxyquinolineHCID 20628273HCID 20628273, compoundHCID 178418339Butyllithium

Product 1

HCID 2922084-[3-(1-Acetyl-4-piperidyl)-1-propenyl]-6-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

Following the procedure of Example 3, 4-chloro-6-methoxyquinoline was reacted with the reaction product of methyl triphenylphosphonium bromide and n-butyllithium. This reaction product was then reacted with N-acetyl-4-piperidine-acetaldehyde to produce 4-[3-(1-acetyl-4-piperidyl)-1-propenyl]-6-methoxyquinoline.

Sources & evidence

ORD record
ord-2ff92e38ff5f4dc69055f54e34cc78ba
Source dataset
uspto-grants-1976_11
Patent number
US03989691

Linked notes

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