Potassium Carbonate → HCID 10427600, compound

HRID 1493552Notes

Reaction equation

HRID 1493552 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH:6]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:22]([CH:24]1[O:26][CH2:25]1)Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:26]1[CH2:25][CH:24]1[CH2:22][N:17]1[CH2:16][CH2:15][N:14]([CH:6]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[C:5]2[CH:20]=[CH:21][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazine

Product 1

HCID 10427600HCID 10427600, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 4,4'-difluorobenzhydrylpiperazine (28.83 g, 100 mmol) in acetonitrile (250 mL) was added to an ice cold mixture of epibromohydrin (9.1 mL, 110 mmol) and anhydrous potassium carbonate (15.2 g, 110 mmol) in acetonitrile (150 mL) over a period of 40 min. The mixture was stirred at room temperature for 100 h, filtered and the solids were washed with methylene chloride. The combined filtrates were concentrated to dryness to give an oil which was eluted through a flash chromatographic silica gel column using 2-3% methanol/methylene chloride to give the title compound as glass, 23.98 (69.6); 300 MHz 1H NMR (CDCl3) δ: 4-6.9 (m, 8H). 4.22 (s. 1H). 3.09 (br m, 1H), 2.8-2.25 (m, 12H); MS 345 (MH+).

Workup

  1. filtrationfiltered
  2. washthe solids were washed with methylene chloride
  3. concentrationThe combined filtrates were concentrated to dryness
  4. customto give an oil which
  5. washwas eluted through a flash chromatographic silica gel column

Sources & evidence

ORD record
ord-1966f78e16054ed892fd5d97d53284cf
Source dataset
uspto-grants-1991_06
Patent number
US05021574

Reaction notes

Loading…