Water → HCID 18357045, compound

HRID 427451Notes

Reaction equation

HRID 427451 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.F[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1.C(=O)([O-])[O-:30].[K+].[K+].O>CS(C)=O>[C:25]([C:24]1[CH:27]=[CH:28][C:21]([O:30][C:6]2[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=2[N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)=[CH:22][CH:23]=1)#[N:26]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 149869034-(4-(4-Pyridyl)piperazin-1-yl)phenol

Product 1

HCID 18357045HCID 18357045, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1-(4-hydroxyphenyl)-4-(4-pyridyl)piperazine (670 mg), 4-fluorobenzonitrile (354 mg) and powdered potassium carbonate (445 mg) was stirred at 95° C. in DMSO (12 ml) for 18 hours. The solution was poured into water (180 ml) to give a precipitate which was filtered, washed with water and dried. The solid was purified by chromatography on alumina (ICN Alumina N 32-63) using 1% methanol in dichloromethane as eluant. This gave a solid which was recrystallised from a mixture of ethyl acetate/isohexane to give 1-(4-cyanophenoxyphenyl)-4-(4-pyridyl)piperazine (126 mg) as a solid. m.p. 180-182° C.

Workup

  1. customto give a precipitate which
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried
  5. customThe solid was purified by chromatography on alumina (ICN Alumina N 32-63)
  6. customThis gave a solid which
  7. customwas recrystallised from a mixture of ethyl acetate/isohexane

Sources & evidence

ORD record
ord-0ac89f56e068400688f09e2298e06305
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

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