Hydrazine → HCID 22174830, compound

HRID 225429Notes

Reaction equation

HRID 225429 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](F)[C:15]=2[C:21](O)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][NH2:25]>CS(C)=O.CCOCC>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:15]=2[CH:21]=[N:24][NH:25]3)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 22174827HCID 22174827, compound

Product 1

HCID 22174830HCID 22174830, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of 4-benzyl-1-(3-fluoro-2-carboxyphenyl)-piperazine (5.96 g, 20.0 mmol) in dimethylsulfoxide (10 mL) and hydrazine (10 mL) is heated at 95° C. under nitrogen for 4 days. The cooled reaction is diluted with ether and washed with a mixture of water and saturated aqueous sodium bicarbonate. The organic layer is further washed sequentially with water and brine dried over MgSO4 and concentrated in vacuo to give a residue. The residue is chromatographed using ethyl acetate as the eluant. The resulting oil is reconcentrated from ether to give a white foam which is stirred under hexanes/ether overnight. The resulting white powder is isolated by suction filtration and washed with hexane to give the title compound 3.11 g, (53% yield), identified by HNMR.

Workup

  1. customThe cooled reaction
  2. washwashed with a mixture of water and saturated aqueous sodium bicarbonate
  3. washThe organic layer is further washed sequentially with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a residue
  7. customThe residue is chromatographed
  8. customto give a white foam which
  9. customThe resulting white powder is isolated by suction filtration
  10. washwashed with hexane

Sources & evidence

ORD record
ord-8a19f2f6fd304ba0902ccdfa1855870d
Source dataset
uspto-grants-2009_07
Patent number
US07557098B2

Reaction notes

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