Sodium Carbonate → 1-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(2-fluoroethyl)piperazine

HRID 419430Notes

Reaction equation

HRID 419430 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:15][CH2:14]1.[F:25][CH:26](I)[CH3:27].C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:20][CH2:21][N:22]([CH2:27][CH2:26][F:25])[CH2:23][CH2:24]2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 23510620IodofluoroethaneHCID 594529121-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine

Product 1

HCID 594527481-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(2-fluoroethyl)piperazineYield 65.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

1-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (0.050 g, 1.41 mmol), 1-fluoroethyliodide (0.229 mL, 2.82 mmol), Na2CO3 (0.179 g, 1.69 mmol) were taken up in acetonitrile (10 mL), heated to 70° C. and stirred overnight. Reaction mixture was cooled and then poured onto prepackaged silica gel cartridge and dried by vacuum suction of air through cartridge and then flash chromatographed to give the title compound of step E (0.370 g, 65%). MS (M+H, ES+) 401.

Workup

  1. customReaction mixture
  2. temperaturewas cooled
  3. additionpoured onto prepackaged silica gel cartridge
  4. customdried by vacuum suction of air through cartridge
  5. customflash chromatographed

Sources & evidence

ORD record
ord-88da2d8f38ba4dcbac4493199108dbd6
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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