2-Chloro-4'-fluoropropiophenone → N-[3-(4-Fluorophenyl)-3-oxopropyl]pipecolic acid methyl ester

HRID 1744895Notes

Reaction equation

[NH:1]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:2]1[C:3]([O:5][CH3:6])=[O:4].Cl[CH2:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[O:15]>>[CH3:6][O:5][C:3](=[O:4])[CH:2]1[CH2:7][CH2:8][CH2:9][CH2:10][N:1]1[CH2:12][CH2:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)=[O:15]

Participants

Reactant 2

HCID 676722-Chloro-4'-fluoropropiophenone

HCID 3463753Methyl pipecolinate

Product 1

HCID 53681476N-[3-(4-Fluorophenyl)-3-oxopropyl]pipecolic acid methyl esterYield 92%

Procedure

N-[3-(4-Fluorophenyl)-3-oxopropyl]pipecolic acid methyl ester was prepared in 92% yield by alkylation of methyl pipecolinate with 3-chloro-4′-fluoropropiophenone (Aldrich) as described in Example 20A (Step 1).

Sources & evidence

ORD record: ord-e751c77486734db788bbca8af135965e
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07019024B2

Reaction notes

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