Water → N-(3,4-dichlorophenyl)-3-nitro-2-piperid-1-yl-5-trifluoromethylbenzamide

HRID 550349Notes

Reaction equation

HRID 550349 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:25])[C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([N+:21]([O-:23])=[O:22])[C:12]=2Cl)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.O>O1CCOCC1.C(OCC)C.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:25])[C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([N+:21]([O-:23])=[O:22])[C:12]=2[N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 86620253N-(3,4-dichlorophenyl)-2-chloro-3-nitro-5-trifluoromethylbenzamide

Product 1

HCID 11854386N-(3,4-dichlorophenyl)-3-nitro-2-piperid-1-yl-5-trifluoromethylbenzamide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of N-(3,4-dichlorophenyl)-2-chloro-3-nitro-5-trifluoromethylbenzamide (0.76 g; 1 eq.) in dioxane (12 ml) is added piperidine (0.4 ml; 2.2 eq.). After stirring for 18 hours at 25° C., 10 ml of water are added and the product is extracted with ethyl acetate. The organic phase is dried and concentrated. The orange oil obtained is dissolved in 2 ml of ethyl ether and 120 ml of hexane. After 3 days at 0° C., the solid is filtered off by suction and dried. 540 mg of N-(3,4-dichlorophenyl)-3-nitro-2-piperid-1-yl-5-trifluoromethylbenzamide are obtained (m.p.=144° C.).

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. customThe orange oil obtained
  5. waitAfter 3 days at 0° C.
  6. filtrationthe solid is filtered off by suction
  7. customdried

Sources & evidence

ORD record
ord-7348f71b401b49b7b8cf85ea219973b1
Source dataset
uspto-grants-2011_05
Patent number
US07947675B2

Reaction notes

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