Water → Olanzapine

HRID 1666937Notes

Reaction equation

HRID 1666937 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.C(#N)C.O.[CH3:22][N:23]1[CH2:28][CH2:27]N[CH2:25][CH2:24]1>>[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[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]3)[C:4]=2[CH:16]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 531671-MethylpiperazineHCID 13552565010H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)

Product 1

HCID 135398745Olanzapine

Conditions

Temperature
120 °C

Procedure

4-Amino-2-methyl-10H-thieno[2,3-b][1,5] benzodiazepine hydrochloride (100 g) is taken in N-methyl piperazine (500 ml). Reaction mixture is heated at 120° C. for 3 hours. The reaction mass is cooled and acetonitrile (400 ml) is added under stirring for 30 minutes. Water (500 ml) is added and the mixture is cooled up to room temperature and stirred to precipitate the solid. The solid is filtered off, washed with acetonitrile (100 ml) and dried at ambient temperature to obtain the crude title compound (64 g).

Workup

  1. customReaction mixture
  2. temperatureThe reaction mass is cooled
  3. temperaturethe mixture is cooled up to room temperature
  4. stirringstirred
  5. customto precipitate the solid
  6. filtrationThe solid is filtered off
  7. washwashed with acetonitrile (100 ml)
  8. customdried at ambient temperature

Sources & evidence

ORD record
ord-5b69675b80d54f02a939234c193e77e9
Source dataset
uspto-grants-2011_10
Patent number
US08044196B2

Reaction notes

Loading…