Sodium Carbonate → 1-(5-Chloro-2-nitro-phenyl)-3-fluoro-piperidine

HRID 646949Notes

Reaction equation

HRID 646949 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[F:18][CH:19]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]1>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N:21]2[CH2:22][CH2:23][CH2:24][CH:19]([F:18])[CH2:20]2)[CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 27591573-Fluoropiperidine

Product 1

HCID 586385391-(5-Chloro-2-nitro-phenyl)-3-fluoro-piperidineYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4-chloro-2-fluoro-1-nitro-benzene (0.30 g, 1.7 mmol) in toluene (5 mL) was treated with solid Na2CO3 (0.40 g, 3.7 mmol) and 3-fluoropiperidine (0.25 mg, 1.8 mmol) and heated to 40° C. for 6 h. The reaction was diluted with EtOAc and washed with water. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the title compound (0.43 g, 98%) as a bright yellow oil. 1H-NMR (CDCl3; 400 MHz): δ 7.76 (d, 1H, J=8.8 Hz), 7.11 (d, 1H, J=2.4 Hz), 6.95 (dd, 1H, J=8.8, 2.4 Hz), 4.86-4.67 (m, 1H), 3.46-3.35 (m, 1H), 3.15-3.06 (m, 2H), 2.99-2.92 (m, 1H), 2.10-1.90 (m, 2H), 1.88-1.69 (m, 2H). LC-MS (ESI, m/z): Calcd. for C11H12ClFN2O2 259.1 (M+H), found 259.1.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-928769dc251c40bab2e8d64e257ec45c
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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