Water → HCID 18357053, compound

HRID 427431Notes

Reaction equation

HRID 427431 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[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([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:15][CH:16]=1)#[N:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 705171-(4-Pyridyl)piperazine

Product 1

HCID 18357053HCID 18357053, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of N-(4-pyridyl)piperazine (9.78 g), 4-fluorobenzonitrile (7.26 g) and powdered potassium carbonate(10 g) was stirred at 100° C. in DMSO (100 ml) overnight. The solution was poured into water (500 ml) to give a precipitate which was filtered and washed with water. The crude solid was dried in a vacuum oven overnight then dissolved in dichloromethane and purified by flash chromatography on alumina (ICN Alumina N 32-63) using an increasing concentration of ethyl acetate in dichloromethane (up to 100% ethyl acetate) as eluant. This gave a solid which was recrystallised from a mixture of ethyl acetate/isohexane to give 1-(4-cyanophenyl)-4-(4-pyridyl)piperazine (7.5 g) as a solid, m.p.157-158° C.; microanalysis. found: C,72.7; H,6.1; N,21.0%; C16H16N4 requires: C,72.7; H,6.1; N,21.2%; NMR: 3.45-3.55(bs, 8H), 6.8-6.9(d, 2H), 7.0-7.1(d, 2H), 7.55-7.65(d, 2H), 8.1-8.2(d, 2H); MS: m/z 265 (MH)+.

Workup

  1. customto give a precipitate which
  2. filtrationwas filtered
  3. washwashed with water
  4. customThe crude solid was dried in a vacuum oven overnight
  5. dissolutionthen dissolved in dichloromethane
  6. custompurified by flash chromatography on alumina (ICN Alumina N 32-63)
  7. customThis gave a solid which
  8. customwas recrystallised from a mixture of ethyl acetate/isohexane

Sources & evidence

ORD record
ord-9cc42ea8089e43688322b41cf7bd9844
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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