Sodium Hydroxide → 2-(4-Methyl-1-piperidinyl)-5-nitro-4'-chlorobenzophenone

HRID 2118819Notes

Reaction equation

HRID 2118819 reaction equation
[OH-].[Na+].Cl[C:4]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:5]=1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:7].[CH3:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>O>[CH3:22][CH:23]1[CH2:28][CH2:27][N:26]([C:4]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:5]=2[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[O:7])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 693814-MethylpiperidineHCID 875720(2-Chloro-5-nitro-phenyl)-(4-chloro-phenyl)-methanone

Product 1

HCID 131055022-(4-Methyl-1-piperidinyl)-5-nitro-4'-chlorobenzophenoneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.024 mole (0.96 g) of NaOH, 25 ml of water, 0.02 mole (5.92 g) of 2,4'-dichloro-5-nitro-benzophenone and of 0.022 mole (2.6 ml) of 4-methylpiperidine is heated to 80° C. for three and a half hours. After cooling the reaction medium to normal temperature the resulting precipitate is filtered, washed in water and dried giving 6.74 g (Yield: 94%) of the expected product. M.P.=138° C. (Ex. 25) The compounds listed hereunder are obtained by reacting, in the same conditions as above, the 2,4'-dichloro-5-nitro-benzophenone with other piperidine derivatives (2-methyl, 3-methyl, 3,5-dimethylpiperidine):

Workup

  1. temperatureAfter cooling the reaction medium to normal temperature the resulting precipitate
  2. filtrationis filtered
  3. washwashed in water
  4. customdried

Sources & evidence

ORD record
ord-02f905cd50574181b9755d5da3eef768
Source dataset
uspto-grants-1987_07
Patent number
US04680402

Reaction notes

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