Tofisopam → HCID 13500543, compound

HRID 905168Notes

Reaction equation

HRID 905168 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:17]3[CH:18]=[C:19]([O:24][CH3:25])[C:20]([O:22][CH3:23])=[CH:21][C:16]=3[CH:15]([CH2:26][CH3:27])[C:14]([CH3:28])=[N:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:17]3[CH:18]=[C:19]([O:24][CH3:25])[C:20]([O:22][CH3:23])=[CH:21][C:16]=3[CH:15]([CH2:26][CH3:27])[CH:14]([CH3:28])[NH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 5502TofisopamHCID 10340Sodium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 13500543HCID 13500543, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A 70% benzene solution of 90 ml (0.6 moles) of NaAlH2 (OCH2CH2OCH3)2 is diluted with 90 ml of benzene. The solution thus-obtained is added, within 20 minutes, under stirring, to a solution of 114.6 g (0.3 moles) of 1-(3,4-dimethoxyphenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodiazepine in 1500 ml of benzene. The inner temperature rises to 33° to 35° C. Then the reaction mixture is heated to boiling, within 30 minutes (the gas evolution ceases), recooled to 20° C., and 450 ml of a 20% sodium hydroxide solution (or, in case of compounds containing phenolic hydroxy groups, an aqueous sodium carbonate solution) are dropped to it. A two-phase light yellowish mixture is obtained.

Workup

  1. customThe solution thus-obtained
  2. additionis added, within 20 minutes
  3. customrises to 33° to 35° C
  4. temperatureThen the reaction mixture is heated
  5. customrecooled to 20° C.
  6. customA two-phase light yellowish mixture is obtained

Sources & evidence

ORD record
ord-7323460dc1e24a87a18d19f5be8683ea
Source dataset
uspto-grants-1983_12
Patent number
US04423044

Reaction notes

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