Dimethyl Sulfoxide → Desmethylolanzapine

HRID 72307Notes

Reaction equation

HRID 72307 reaction equation
Cl.[NH2:2][C:3]1[C:4]2[CH:16]=[C:15]([CH3:17])[S:14][C:5]=2[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1.CS(C)=O.C1(C)C=CC=CC=1.[NH:29]1[CH2:34][CH2:33]N[CH2:31][CH2:30]1>O>[CH3:17][C:15]1[S:14][C:5]2[NH:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[N:9]=[C:3]([N:2]3[CH2:33][CH2:34][NH:29][CH2:30][CH2:31]3)[C:4]=2[CH:16]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 4837PiperazineHCID 13552565010H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)

Product 1

HCID 135446209DesmethylolanzapineYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

Starting material C (prepared according to the above, 140 mg, 0.53 mmol) was added to a mixture of dry dimethyl sulfoxide (1 ml), dry toluene (1 ml), and piperazine (140 mg, 1.6 mmol). The stirred solution was then heated at 125° C. under nitrogen for 5 h and cooled to room temperature. Then distilled water (2 ml) was added, while the temperature is kept below 25° C. After stirring at 5° C. for 30 minute, the suspension was cooled overnight and the solid D was filtered, washed with chilled water, and dried at 70° C. under reduced pressure; yield 69%.

Workup

  1. customprepared
  2. temperaturecooled to room temperature
  3. customis kept below 25° C
  4. temperaturethe suspension was cooled overnight
  5. filtrationthe solid D was filtered
  6. washwashed with chilled water
  7. customdried at 70° C. under reduced pressure

Sources & evidence

ORD record
ord-1d4501d22a784543b7e36cf1d37b9bcb
Source dataset
uspto-grants-2014_09
Patent number
US08828993B2

Reaction notes

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