1-Propanol → Olanzapine

HRID 251391Notes

Reaction equation

HRID 251391 reaction equation
[NH2:1][C:2]1[C:3]2[CH:15]=[C:14]([CH3:16])[S:13][C:4]=2[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[CH3:17][N:18]1[CH2:23][CH2:22]N[CH2:20][CH2:19]1.C(O)CC>O>[CH3:16][C:14]1[S:13][C:4]2[NH:5][C:6]3[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=3[N:8]=[C:2]([N:1]3[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]3)[C:3]=2[CH:15]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 531671-MethylpiperazineHCID 135446208Olanzamine

Product 1

HCID 135398745OlanzapineYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

4-Amino-2-methyl-10H-thieno-[2,3-b][1,5]benzodiazepine (5 g, 0.02 mol), N-methylpiperazine (12.5 mL, 2.5 vol) and 1-propanol (15 mL, 3 vol) were charged into a three-necked round bottom flask equipped with a reflux condenser, overhead stirrer, and thermometer. The reaction mixture was heated slowly to 110° C. under a nitrogen atmosphere and then refluxed overnight. The reaction mixture was cooled to below 50° C. whereupon water (15 mL, 3 volumes) was added to precipitate out the solid, which was isolated by Buchner filtration. The resulting light yellow solid was washed twice with water (5 mL) and dried to afford olanzapine in 89% yield (5.22 g).

Workup

  1. customequipped with a reflux condenser, overhead stirrer
  2. temperaturerefluxed overnight
  3. additionwas added
  4. customto precipitate out the solid
  5. customwhich was isolated by Buchner filtration
  6. washThe resulting light yellow solid was washed twice with water (5 mL)
  7. customdried

Sources & evidence

ORD record
ord-28d0944192d34f2387a679d54825d7ad
Source dataset
uspto-grants-2011_01
Patent number
US07863442B2

Reaction notes

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