Chloroacetonitrile → HCID 58189053, compound

HRID 1423239Notes

Reaction equation

HRID 1423239 reaction equation
[CH2:1]([CH:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:29][C:30]#[N:31].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[CH2:29][C:30]#[N:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 66824803HCID 66824803, compound

Product 1

HCID 58189053HCID 58189053, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Into a 25 mL screw-cap vial were added 3-benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (104 mg, 0.28 mmol), chloroacetonitrile (25 μL, 0.39 mmol), K2CO3 (88 mg, 0.64 mmol), and DMF (2 mL). The reaction mixture was heated at 60° C. for 8 h then cooled to room temperature. The reaction mixture was concentrated and adsorbed onto silica gel then purified by silica gel flash chromatography with a 0-10% MeOH/CH2Cl2 gradient to afford product as a light green solid (65 mg, 57%). LC/MS (Method B) 3.84 min, [M+1]+ 406.

Workup

  1. customInto a 25 mL screw-cap vial
  2. temperaturethen cooled to room temperature
  3. concentrationThe reaction mixture was concentrated
  4. customthen purified by silica gel flash chromatography with a 0-10% MeOH/CH2Cl2 gradient

Sources & evidence

ORD record
ord-1193ace27336461d93ae47e30284b572
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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