Sodium hydride → HCID 17986267, compound

HRID 268721Notes

Reaction equation

HRID 268721 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N:11]1([CH2:17][CH2:18][CH2:19][OH:20])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[H-].[Na+]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([O:20][CH2:19][CH2:18][CH2:17][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 66032Piperidine-1-propanolHCID 1090002-Chloro-4-fluorobenzonitrile

Product 1

HCID 17986267HCID 17986267, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-4-fluorobenzonitrile (5.0 g) and 3-(1-piperidinyl)-1-propanol (3.4 g) were stirred in DMSO (70 ml) at rt under argon. Sodium hydride (60% wt in mineral oil, 1.976 g) was then added and the reaction stirred at rt for 5 h. The reaction mixture was diluted with ethyl acetate (200 ml), washed with saturated sodium hydrogen carbonate (100 ml), water (3×100 ml), brine (100 ml), dried (MgSO4) and evaporated. The crude product was then purified by column chromatography [silica gel, step gradient 0-10% MeOH (containing 10% 0.880 ammonia solution) in DCM)] and fractions containing pure product were combined and evaporated to give the title compound (D26) as a white solid (6.29 g). MS electrospray (+ion) 279/281 (MH+).

Workup

  1. washwashed with saturated sodium hydrogen carbonate (100 ml), water (3×100 ml), brine (100 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe crude product was then purified by column chromatography [silica gel, step gradient 0-10% MeOH (containing 10% 0.880 ammonia solution) in DCM)] and fractions
  5. additioncontaining pure product
  6. customevaporated

Sources & evidence

ORD record
ord-91261d33efb34fd5b56ee802caa105bb
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

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