Hydrochloric Acid → HCID 13336317, compound

HRID 638190Notes

Reaction equation

HRID 638190 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.Cl.O>C(Cl)Cl.CCOCC>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]2)=[CH:11][CH:12]=1)([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 27375314-Amino-1-methylpiperidine

Product 1

HCID 13336317HCID 13336317, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-amino-1-methylpiperidine (4.82 g, 32.3 mmol) and 4-fluoronitrobenzene (4.56 g, 32.3 mmol) is heated at 100° C. on an oil bath over a period of 7 hours. After cooling, the reaction mixture is mixed with 2N hydrochloric acid (20 ml) and water (20 ml) and shaken with ether. The acidic layer is neutralized with conc. ammoniac solution and shaken with methylene chloride. The methylene chloride layer is washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is crystallized from ether-petroleum ether to give 4-(4-nitroanilino)-1-methylpiperidine (4.27 g) as crystals melting at 153° to 155° C. The yield is 56%.

Workup

  1. temperatureAfter cooling
  2. washThe methylene chloride layer is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is crystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-f021127008b94e5a8bfac43704d7255b
Source dataset
uspto-grants-1985_12
Patent number
US04560684

Reaction notes

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