Water → HCID 67413381, compound

HRID 331122Notes

Reaction equation

HRID 331122 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:29]1[C:34]([C:35]#[N:36])=[CH:33][CH:32]=[CH:31][N:30]=1.O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:29]3[C:34]([C:35]#[N:36])=[CH:33][CH:32]=[CH:31][N:30]=3)[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 810792-ChloronicotinonitrileHCID 23023142HCID 23023142, compound

Product 1

HCID 67413381HCID 67413381, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(3-hydroxy-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (300 mg, 1.0 mmol) in DMSO (5.0 mL) were added Cs2CO3 (660 mg, 2.0 mmol) and 2-chloro-3-pyridinecarbonitrile (172 mg, 1.2 mmol). The mixture was heated at 60° C. for 90 min. The reaction mixture was cooled to rt, poured into water, and extracted with EtOAc (3×). The organic layer was separated and dried (Na2SO4). The crude residue was purified (FCC) to give 4-[3-(3-cyano-pyridin-2-yloxy)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester (229 mg, 56%).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with EtOAc (3×)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-30c3a8a36aaa4becba4191e245c3d9c0
Source dataset
uspto-grants-2014_11
Patent number
US08877769B2

Reaction notes

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