Sodium Carbonate → 1-[3-(Ethyloxy)-4-nitrophenyl]-4-[1-(2-fluoroethyl)-4-piperidinyl]piperazine

HRID 419398Notes

Reaction equation

HRID 419398 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:15][CH2:14]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2].I[CH2:26][CH2:27][F:28].C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:13]2[CH2:14][CH2:15][N:16]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:26][CH2:27][F:28])[CH2:21][CH2:20]3)[CH2:17][CH2:18]2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 594528881-[3-(Ethyloxy)-4-nitrophenyl]-4-(4-piperidinyl)piperazine

Product 1

HCID 594526551-[3-(Ethyloxy)-4-nitrophenyl]-4-[1-(2-fluoroethyl)-4-piperidinyl]piperazineYield 65.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1-[3-(ethyloxy)-4-nitrophenyl]-4-(4-piperidinyl)piperazine (0.28 g, 0.83 mmol) and 1-iodo-2-fluoroethane (0.29 g, 1.67 mmol) in acetonitrile (17 mL) was added Na2CO3 (0.106 g, 1.0 mmol). The reaction was stirred under N2 and heated to reflux for 4 h. The temperature was lowered to 75° C. and the reaction was stirred overnight (approximately 16 h). The reaction was cooled to rt and then concentrated under vacuum. The residue was purified by silica gel chromatography to give the title compound of step B (206 mg, 0.54 mmol, 65%) as a yellow solid. MS (ESI): 381 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customwas lowered to 75° C.
  4. stirringthe reaction was stirred overnight (approximately 16 h)
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cc8a9d14ae4e4715a3e4ef22479c25b2
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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