Dimethyl Sulfoxide → HCID 67608172, compound

HRID 2280850Notes

Reaction equation

HRID 2280850 reaction equation
F[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:16][CH:17]1[CH2:22][NH:21][CH2:20][CH2:19][NH:18]1.C(N(CC)CC)C.CS(C)=O>O>[CH3:16][CH:17]1[NH:18][CH2:19][CH2:20][N:21]([C:2]2[CH:15]=[CH:14][C:5]([C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:7])=[CH:4][CH:3]=2)[CH2:22]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 660572-MethylpiperazineHCID 676634-Fluorobenzophenone

Product 1

HCID 67608172HCID 67608172, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a 1 L two-neck flask was added 4-fluorobenzophenone (100 g) and 2-methyl piperazine (60 g), triethyl amine (160 mL) and dimethyl sulfoxide (200 mL). The flask was seated in oil bath. The oil bath was heated to 100° C. for 24 hours. The mixture was cooled to room temperature and then poured into water (300 mL). The mixture was extracted with chloroform (300 mL). The bottom layer was separated and washed with water (500 mL) and brine (300 mL). The final solution was condensed and the residue was filtered off a silica gel plug. The major fraction was condensed to afford yellow oily 4-(3-methylpiperazino)benzophenone (130 g).

Workup

  1. customThe flask was seated in oil bath
  2. temperatureThe mixture was cooled to room temperature
  3. extractionThe mixture was extracted with chloroform (300 mL)
  4. customThe bottom layer was separated
  5. washwashed with water (500 mL) and brine (300 mL)
  6. customcondensed
  7. filtrationthe residue was filtered off a silica gel plug
  8. customcondensed

Sources & evidence

ORD record
ord-196fdf2efb3a4ad7b240aeeabfd50c3b
Source dataset
uspto-grants-2015_09
Patent number
US09139552B2

Reaction notes

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