Potassium Cyanide → HCID 89938218, compound

HRID 2200357Notes

Reaction equation

HRID 2200357 reaction equation
CS(O[CH2:6][CH2:7][CH:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH3:9])(=O)=O.[C-:23]#[N:24].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([N:13]2[CH2:14][CH2:15][N:10]([CH:8]([CH3:9])[CH2:7][CH2:6][C:23]#[N:24])[CH2:11][CH2:12]2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 89938217HCID 89938217, compound

Product 1

HCID 89938218HCID 89938218, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-(4-(4-fluorophenyl) piperazin-1-yl)butyl methanesulfonate (4.5 g, 13.62 mmol) in N,N-dimethylformamide (30 ml) was added potassium cyanide (2.66 g, 40.9 mmol) at 25° C. under nitrogen atmosphere. The reaction mixture was stirred at 50° C. for 15 h. Progress of reaction was monitored by TLC. The reaction mixture was diluted with ethyl acetate (150 ml) and washed with water (4×50 ml). The organic layer was dried over sodium sulphate and concentrated under reduced pressure to get oily compound. The resulting crude compound was purified over silica gel (100-200 mesh) by flash chromatography using 30% ethyl acetate in hexane as an eluent to obtain title compound (2.6 g).

Workup

  1. customProgress of reaction
  2. washwashed with water (4×50 ml)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto get oily compound
  6. customThe resulting crude compound was purified over silica gel (100-200 mesh) by flash chromatography

Sources & evidence

ORD record
ord-ec23c632d2df4e5d8030b66971777226
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

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