Dimethyl Sulfoxide → 1'-[3-(Methyloxy)-4-nitrophenyl]-1,4'-bipiperidine

HRID 419329Notes

Reaction equation

HRID 419329 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].[N:13]1([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].CS(C)=O>O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:22]2[CH2:23][CH2:24][CH:19]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:20][CH2:21]2)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 786071,4'-BipiperidineHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 587483781'-[3-(Methyloxy)-4-nitrophenyl]-1,4'-bipiperidineYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5-fluoro-2-nitrophenyl methyl ether (26.0 g, 152 mmol), 1,4′-bipiperidine (25.5 g, 152 mmol) and K2CO3 (22.9 g, 166 mmol) was added DMSO (260 mL). The mixture was stirred at room temperature for 3 days. The mixture was poured into H2O (1000 mL) and the H2O washed with EtOAc (2×500 mL). The EtOAc washes were combined and washed with H2O (2×500 mL). The ether layer was dried (MgSO4), filtered, and rotovaped down to give the title compound (47.9 g, 150 mmol, 99%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.98 (d, J=9.5 Hz, 1H), 6.40 (dd, J=9.5 and 2.6 Hz, 1H), 6.29 (d, J=2.6 Hz, 1H), 3.99-3.93 (m, 2H), 3.93 (s, 3H), 2.98-2.89 (m, 2H), 2.58-2.48 (m, 5H), 1.99-1.90 (m, 2H), 1.70-1.55 (m, 8H), 1.48-1.40 (m, 2H).

Workup

  1. washthe H2O washed with EtOAc (2×500 mL)
  2. washwashed with H2O (2×500 mL)
  3. dry with materialThe ether layer was dried (MgSO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-d6e40fb32e6e43c4b7351fd1a0f3d7ad
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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