Potassium Carbonate → Ethyl 4-(3-(1-methylpiperidin-3-yl)phenylamino)-3-nitrobenzoate

HRID 324737Notes

Reaction equation

HRID 324737 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH3:16][N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([C:23]2[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=2)[NH2:26])[CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:16][N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([C:23]2[CH:24]=[C:25]([NH:26][C:2]3[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=3[N+:13]([O-:15])=[O:14])[CH:27]=[CH:28][CH:29]=2)[CH2:18]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 1268247Ethyl 4-chloro-3-nitrobenzoateHCID 22741929HCID 22741929, compound

Product 1

HCID 22741906Ethyl 4-(3-(1-methylpiperidin-3-yl)phenylamino)-3-nitrobenzoateYield 98%

Conditions

Temperature
70 °C

Procedure

A mixture of 1c (5.7 g, 25 mmol), 2j (3.8 g, 20 mmol) and potassium carbonate (3.45 g, 25 mmol) was heated to 70° C. under a stream of nitrogen. The resulting melt was stirred at 70° C. overnight. The reaction mixture was partitioned between water and ethyl acetate and the organic phase was extracted with diluted hydrochloric acid (4M). The aqueous phase was rendered alkaline by addition of aqueous sodium hydroxide (4M) and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure to leave ethyl 4-(3-(1-methylpiperidin-3-yl)phenylamino)-3-nitrobenzoate (7.5 g, 98%) as an oil.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionthe organic phase was extracted with diluted hydrochloric acid (4M)
  3. additionby addition of aqueous sodium hydroxide (4M)
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1d471ddf64eb42a2b9b033a10de4e4a2
Source dataset
uspto-grants-2001_04
Patent number
US06218547B1

Reaction notes

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