Water → 1-Aminocarbonyl-4-(4-nitrophenoxy)-4-phenylpiperidine

HRID 1721854Notes

Reaction equation

HRID 1721854 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+]([NH:26][C:27](N)=[O:28])([O-])=O.O>C(O)C>[NH2:26][C:27]([N:12]1[CH2:11][CH2:10][C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:22][CH:21]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:14][CH2:13]1)=[O:28]

Participants

5

Reactant 3

HCID 962WaterHCID 62372NitroureaHCID 200299564-(4-Nitrophenoxy)-4-phenylpiperidine

Product 1

HCID 146499891-Aminocarbonyl-4-(4-nitrophenoxy)-4-phenylpiperidineYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 4.0 g of 4-(4-nitrophenoxy)-4-phenylpiperidine in 50 ml of 95% ethanol was added 1.68 g of nitrourea in 50 ml of 95% ethanol. The reaction mixture was refluxed for two hours and then poured into 200 ml of water. The aqueous suspension was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting solid was purified by high pressure liquid chromatography (silica gel; elution with 5% methanol/dichloromethane) to yield 4.04 g (91.20%) of 1-aminocarbonyl-4-(4-nitrophenoxy)-4-phenylpiperidine, m.p. 203°-206° C.

Workup

  1. temperatureThe reaction mixture was refluxed for two hours
  2. extractionThe aqueous suspension was extracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid was purified by high pressure liquid chromatography (silica gel; elution with 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-ce2055ac1c994bf98d65d3ff4fd7683c
Source dataset
uspto-grants-1989_08
Patent number
US04853384

Reaction notes

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