Water → HCID 19350708, compound

HRID 1636231Notes

Reaction equation

HRID 1636231 reaction equation
[CH3:1][C:2]1[S:22][C:5]2[NH:6][C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.[H-].[Na+].[CH:25](Br)([CH3:27])[CH3:26].O>CN(C)C=O>[CH3:1][C:2]1[S:22][C:5]2[N:6]([CH:25]([CH3:27])[CH3:26])[C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 135398745Olanzapine

Product 1

HCID 19350708HCID 19350708, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine (3.12 g) in dry dimethylformamide (50 ml) was added sodium hydride (0.63 g, 50% dispersion). The reaction mixture was stirred for 30 minutes at room temperature, then 30 minutes at 60-70° C. The reaction was cooled to 40° C., isopropyl bromide (1.13 ml) added and left for one hour. Water was added and the reaction extracted with ethyl acetate, washed with water, dried and evaporated under reduced pressure. Chromatography using 2% methanol/dichloromethane and flash silica gave the title compound, m.p. 120-121° C. Similarly prepared from the same starting material were:

Workup

  1. custom30 minutes
  2. customat 60-70° C
  3. temperatureThe reaction was cooled to 40° C.
  4. waitleft for one hour
  5. extractionthe reaction extracted with ethyl acetate
  6. washwashed with water
  7. customdried
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4a105ab238ff4f9d943ce55620c2f70e
Source dataset
uspto-grants-2000_03
Patent number
US06034078

Reaction notes

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