Water → HCID 11854634, compound

HRID 550356Notes

Reaction equation

HRID 550356 reaction equation
Br[C:2]1[C:3]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:4]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)=[O:6].[C:29]([Cu])#[N:30].O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:29]([C:2]1[C:3]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)=[C:4]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)=[O:6])#[N:30]

Participants

6

Reactant 3

HCID 962WaterHCID 11854633HCID 11854633, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 11854634HCID 11854634, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-N-(3,4-dichlorophenyl)-2-piperid-1-yl-5-trifluoromethylbenzamide, Example 3 (620 mg; 1 eq.) in DMF (10 ml, degassed for 1 hour with nitrogen), are added CuCN (200 mg; 1.8 eq.) and Pd(PPh3)4 (58 mg; 0.04 eq.). After refluxing for 3 hours under a nitrogen atmosphere, the reaction medium is cooled and poured into 20 ml of water. The product is extracted with ethyl acetate. After washing with water and then with saturated NaCl solution, the organic phase is dried over Na2SO4 and concentrated under vacuum. The oil obtained is purified by chromatography on silica (eluent: 9/1 heptane/EtOAc). 310 mg of 3-cyano-N-(3,4-dichlorophenyl)-2-piperid-1-yl-5-trifluoromethylbenzamide are obtained (white solid: m.p.=175° C.)

Workup

  1. temperatureAfter refluxing for 3 hours under a nitrogen atmosphere
  2. temperaturethe reaction medium is cooled
  3. extractionThe product is extracted with ethyl acetate
  4. washAfter washing with water
  5. dry with materialwith saturated NaCl solution, the organic phase is dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe oil obtained
  8. customis purified by chromatography on silica (eluent: 9/1 heptane/EtOAc)

Sources & evidence

ORD record
ord-0db39ca238cd44aa81e98ba0655e7ff8
Source dataset
uspto-grants-2011_05
Patent number
US07947675B2

Reaction notes

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