Dimethylformamide → HCID 66711380, compound

HRID 1261999Notes

Reaction equation

HRID 1261999 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH2:2]1.F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[Cl-].[NH4+]>>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([N:1]2[CH2:6][CH2:5][CH2:4][CH:3]([N:7]3[CH2:8][CH2:9][O:10][CH2:11][CH2:12]3)[CH2:2]2)=[CH:15][CH:16]=1)([O-:22])=[O:21]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 21327197HCID 21327197, compound

Product 1

HCID 66711380HCID 66711380, compound

Conditions

Temperature
100 °C

Procedure

4-Piperidin-3-yl-morpholine (1.70 g, 9.98 mmol), 4-Fluoronitrobenzene (1.3 g, 9.1 mmol) and Potassium carbonate (3.14 g, 22.7 mmol) were dissolved in N,N-Dimethylformamide (60 mL, 800 mmol). The reaction mixture was then heated at 100° C. and was allowed to stir overnight. The reaction mixture was poured over saturated ammonium chloride and organics were extracted with dichloromethane/ethyl acetate. Combined extracts were then dried over sodium sulfate, filtered and reduced. The crude reaction mixture was then purified by Isco flash column chromatography (hexanes/ethyl acetate eluent). Combined fractions were reduced and dried under vacuum to afford 4-[1-(4-Nitro-phenyl)-piperidin-3-yl]-morpholine. (M+H)=292.6. 1H NMR (400 MHz, DMSO, d6) δ 8.02 (d, 2H, J=9.45 Hz), 6.99 (d, 2H, J=9.48 Hz), 4.08 (m, 1H), 3.98 (m, 1H), 3.56 (t, 4H, J=4.56 Hz), 2.96 (m, 2H), 2.62 (m, 2H), 2.52 (m, 2H), 2.31 (m, 1H), 1.93 (m, 1H), 1.80 (m, 1H), 1.50 (m, 2H).

Workup

  1. extractionorganics were extracted with dichloromethane/ethyl acetate
  2. dry with materialCombined extracts were then dried over sodium sulfate
  3. filtrationfiltered
  4. customThe crude reaction mixture
  5. customwas then purified by Isco flash column chromatography (hexanes/ethyl acetate eluent)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-8635ea30c3a947cb9984b4a1b15ab97b
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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