Water → HCID 18357144, compound

HRID 427450Notes

Reaction equation

HRID 427450 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[F:13][C:14]1[CH:28]=[CH:27][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=2)=O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[F:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:10]2[CH2:9][CH2:8][N:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH2:12][CH2:11]2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 95824,4'-DifluorobenzophenoneHCID 11430Potassium CarbonateHCID 705171-(4-Pyridyl)piperazine

Product 1

HCID 18357144HCID 18357144, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of N-(4-pyridyl)piperazine (8.15 g), 4,4′-difluorobenzophenone (13.1 g) and powdered potassium carbonate (9.12 g) was stirred at 95° C. in DMSO (100 ml) overnight. The solution was poured into water (1500 ml) to give a precipitate which was filtered, washed with water and dried. The solid (7.82 g) was stirred in trifluoroacetic acid (25 ml) under argon with triethylsilane (10 ml) for 18 hours. The solution was poured into water (315 ml), taken to pH 12 with sodium hydroxide solution and extracted with dichloromethane (2×300 ml). The combined dichloromethane extracts were washed with water, dried (Na2SO4) and evaporated to give a residue which was purified by chromatography on alumina (ICN Alumina N 32-63) using 0.5% methanol in dichloromethane as eluant. The solid obtained was recrystallised from a mixture of ethyl acetate/isohexane to give 1-(4-fluorobenzylphenyl)-4-(4-pyridyl)piperazine (350 mg) as a solid, m.p. 110-111° C.

Workup

  1. customto give a precipitate which
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried
  5. additionThe solution was poured into water (315 ml)
  6. extractionextracted with dichloromethane (2×300 ml)
  7. washThe combined dichloromethane extracts were washed with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customto give a residue which
  11. customwas purified by chromatography on alumina (ICN Alumina N 32-63)
  12. customThe solid obtained
  13. customwas recrystallised from a mixture of ethyl acetate/isohexane

Sources & evidence

ORD record
ord-e69b2bae395e417a816e539400768698
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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