Tofisopam → HCID 13500543, compound

HRID 905169Notes

Reaction equation

HRID 905169 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].[BH4-].[Na+]>C(O)(=O)C.O>[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 2

HCID 5502TofisopamHCID 4311764Sodium borohydride

Product 1

HCID 13500543HCID 13500543, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 3.82 g (0.01 mole) of 1-(3,4-dimethoxyphenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodiazepine in 38 ml of glacial acetic acid a solution of 3 g of sodium borohydride in 10 ml of water is dropped within 2 hours at 3° to 8° C., under stirring. Then the reaction mixture is stirred further for 5 hours at 20° to 25° C. and evaporated in vacuo. The residue (18 g) is dissolved in 30 ml of water, and 10 ml of a 40% sodium hydroxide solution are added. The product separated in soft form crystallizes after cooling. Yield: 3.1 g. The product shrinks from 75° C. The pure compound can be obtained by proceeding as described in Example 2. Yield: 2.29 g. M.p.: 120° to 122° C. Molecular formula: C22H28N2O4.

Workup

  1. stirringThen the reaction mixture is stirred further for 5 hours at 20° to 25° C.
  2. customevaporated in vacuo
  3. dissolutionThe residue (18 g) is dissolved in 30 ml of water
  4. addition10 ml of a 40% sodium hydroxide solution are added
  5. customThe product separated in soft form
  6. customcrystallizes
  7. temperatureafter cooling
  8. customshrinks from 75° C
  9. customThe pure compound can be obtained

Sources & evidence

ORD record
ord-16debc46ecba47f7a2292193fbfaa922
Source dataset
uspto-grants-1983_12
Patent number
US04423044

Reaction notes

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