Acrylonitrile → HCID 58188973, compound

HRID 1423241Notes

Reaction equation

HRID 1423241 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.[C:28](#[N:31])[CH:29]=[CH2:30].C(N(CC)CC)C>CO>[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[CH2:30][CH2:29][C:28]#[N:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 66824803HCID 66824803, compound

Product 1

HCID 58188973HCID 58188973, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Into a 25 mL screw-cap vial were added 3-benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (206 mg, 0.562 mmol), acrylonitrile (55 μL, 0.83 mmol), triethylamine (500 μL), and MeOH (5 mL). The reaction mixture was heated at 60° C. for 4 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 the title compound as a yellow waxy solid (181 mg, 77%). LC/MS (Method B) 2.77 min, [M+1]+ 420.

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-9c857b7da29f46ee9a473bf6be57f650
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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