4-Fluorobenzamide → HCID 58119379, compound

HRID 1187442Notes

Reaction equation

HRID 1187442 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][C:13]([CH:15]1[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]1)=O>CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][CH:12]=[C:13]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 715724-FluorobenzamideHCID 18187487tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylate

Product 1

HCID 58119379HCID 58119379, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-fluorobenzamide (4.54 g, 32.7 mmol) and t-butyl 4-(bromoacetyl)-piperidine-1-carboxylate (5.0 g, 16.3 mmol) in DMF (40 mL) was heated at 145° C. for 16 h. Upon completion of the reaction, the solution was allowed to cool to rt and concentrated to a dark oil. The oil was purified by reverse phase HPLC to afford the title compound (760 mg). LC/MS: m/e 247.08 (M+H)+.

Workup

  1. customUpon completion of the reaction
  2. concentrationconcentrated to a dark oil
  3. customThe oil was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-48297255021e4444aff7c422a887eb59
Source dataset
uspto-grants-2014_03
Patent number
US08673941B2

Reaction notes

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