Sodium Carbonate → N-(1-benzylpiperidin-4-yl)-2-nitro-4-methylsulphonylaniline

HRID 1592995Notes

Reaction equation

HRID 1592995 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.F[C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27].C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O>[CH2:8]([N:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][C:17]=2[N+:26]([O-:28])=[O:27])[CH2:3][CH2:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 3131371-Fluoro-4-methanesulfonyl-2-nitrobenzeneHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 9281505N-(1-benzylpiperidin-4-yl)-2-nitro-4-methylsulphonylanilineYield 98.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

4-Amino-1-benzylpiperidine (87 g) was added slowly during 20 minutes to a stirred mixture of 2-fluoro-5-methylsulphonyl-nitrobenzene (100 g) and anhydrous sodium carbonate (35 g) in 500 mL DMSO, the internal temperature rose from 20° C. to 50° C. The mixture was stirred at 90° C. for 12 hours, then poured into ice/water and the yellow solid was filtered off, redissolved in dichloromethane, dried and evaporated to give 175 g N-(1-benzylpiperidin-4-yl)-2-nitro-4-methylsulphonylaniline.

Workup

  1. customrose from 20° C. to 50° C
  2. filtrationthe yellow solid was filtered off
  3. dissolutionredissolved in dichloromethane
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-cdb0c86b30f8408d9f59b887e5cbf963
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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