Methanol → Olanzamine

HRID 1350360Notes

Reaction equation

HRID 1350360 reaction equation
Cl.[CH3:2][C:3]1[S:12][C:11]2[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]=[C:6]([NH2:17])[C:5]=2[CH:4]=1.[OH-].[Na+].CO>O>[CH3:2][C:3]1[S:12][C:11]2[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]=[C:6]([NH2:17])[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 13552565010H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)

Product 1

HCID 135446208OlanzamineYield 92.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Slurry 2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene-10-ylamine hydrochloride (5.2 g, 19.5 mmol) in water and add 1N sodium hydroxide (19.5 mL, 19.5 mmol). Add methanol to facilitate stirring and extract with methylene chloride. Purify the methylene chloride extracts by silica gel chromatography using 7N ammonia in methanol-methylene chloride (5%) as the eluent to give (4.13 g, 92%) of the title compound.

Workup

  1. extractionextract with methylene chloride
  2. customPurify the methylene chloride

Sources & evidence

ORD record
ord-646e9e5d86c443388098ec0642ff6cb1
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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