Potassium Carbonate → HCID 22277827, compound

HRID 1064029Notes

Reaction equation

HRID 1064029 reaction equation
[F:1][C:2]1[N:7]=[C:6]([F:8])[C:5]([F:9])=[C:4](F)[C:3]=1[F:11].[CH2:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:8][C:6]1[C:5]([F:9])=[C:4]([N:22]2[CH2:23][CH2:24][N:19]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:20][CH2:21]2)[C:3]([F:11])=[C:2]([F:1])[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69690PentafluoropyridineHCID 759941-Benzylpiperazine

Product 1

HCID 22277827HCID 22277827, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of pentafluoropyridine (1.76 ml, 16.0 mmol) and 1-benzylpiperazine (2.64 g, 15.0 mmol) in DMSO (20 ml) was added potassium carbonate (4.20 g, 30.4 ml). The suspension was heated to 100° C. and stirred for five hours and allowed to cool to ambient temperature, poured onto water and then extracted with DCM. The extract was washed with brine, water, and dried. Volatile material was removed by evaporation to give the title compound (4.59 g) as an oil. NMR (CDCl3) 2.58 (m, 4H), 3.52 (m, 4H), 3.57 (s, 2H), 7.24-7.38 (m, 5H and CDCL3); m/z 326.

Workup

  1. temperatureto cool to ambient temperature
  2. additionpoured onto water
  3. extractionextracted with DCM
  4. washThe extract was washed with brine, water
  5. customdried
  6. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-424b6da6318d4fc7ba6929d8963ed735
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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