Diisopropylethylamine → 3-chloro-N-(1-methyl-4-piperidyl)-4-nitro-benzamide

HRID 2234374Notes

Reaction equation

HRID 2234374 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](Cl)=[O:6].C(N(CC)C(C)C)(C)C.[NH2:23][CH:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([NH:23][CH:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1)=[O:6]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 190776143-Chloro-4-nitrobenzoyl chloride2×

Product 1

HCID 686867193-chloro-N-(1-methyl-4-piperidyl)-4-nitro-benzamideYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-chloro-4-nitro-benzoyl chloride (Intermediate 54; 2.2 g, 10.00 mmol) was dissolved in DCM (20 mL) and N,N-diisopropylethylamine (2.095 mL, 12.00 mmol) added. The mixture was cooled in an ice/water bath and 4-amino-1-methylpiperidine (Fluorochem; 1.14 g, 10.00 mmol) in DCM (10 mL) added dropwise. The mixture was allowed to warm to room temperature and stirred for 0.5 hr. A white precipitate resulted. The reaction mixture was washed with 2N NaOH, filtered and the filter cake washed with water and dried on a sinter over the weekend to give the title compound as a white solid (1.80 g, 60%) as a white solid.

Workup

  1. temperatureThe mixture was cooled in an ice/water bath
  2. customA white precipitate resulted
  3. washThe reaction mixture was washed with 2N NaOH
  4. filtrationfiltered
  5. washthe filter cake washed with water
  6. customdried on a sinter over the weekend

Sources & evidence

ORD record
ord-d8a0ad712d5e4d69b2978c7dce6a23db
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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