HCID 59204985, compound → 1-(2-Fluoro-4-nitrophenyl)piperidine-4-ylmethylamine

HRID 2241904Notes

Reaction equation

HRID 2241904 reaction equation
C(=[N:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=2[F:25])[CH2:12][CH2:11]1)C1C=CC=CC=1>Cl>[F:25][C:17]1[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:16]=1[N:13]1[CH2:12][CH2:11][CH:10]([CH2:9][NH2:8])[CH2:15][CH2:14]1

Participants

3

Reactant 1

HCID 59204985HCID 59204985, compound

Product 1

HCID 592050221-(2-Fluoro-4-nitrophenyl)piperidine-4-ylmethylamineYield 98.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1N aqueous hydrochloric acid (20 ml) was added to benzylidene[1-(2-fluoro-4-nitrophenyl)piperidine-4-ylmethyl]amine (compound of Reference Example 21; 1.15 g, 3.36 mmol), and the mixture was refluxed for 6 hours. The reaction mixture was washed with ethyl acetate and adjusted to pH=12 by addition of 2N aqueous sodium hydroxide. The water layer was saturated with sodium chloride and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (0.838 g, 98%) as a yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. washThe reaction mixture was washed with ethyl acetate
  3. additionadjusted to pH=12 by addition of 2N aqueous sodium hydroxide
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-05a0af01464f43a8a51e86e304bd3a47
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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