Hydrochloric Acid → 9,10-Dihydro-9-methyl-4-phenethyl-4H-thieno[3,4-b][1,5]benzodiazepine

HRID 1863162Notes

Reaction equation

HRID 1863162 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13](=O)[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2=[CH:22][S:23][CH:24]=[C:4]2[C:3]1=O.B.Cl.[OH-].[Na+]>O1CCCC1>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2=[CH:22][S:23][CH:24]=[C:4]2[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14798Sodium HydroxideHCID 203922324,9-Dihydro-9-methyl-4-phenylacetyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 203922399,10-Dihydro-9-methyl-4-phenethyl-4H-thieno[3,4-b][1,5]benzodiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 6.0 g. of 4,9-dihydro-9-methyl-4-phenylacetyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 100 ml. of dried tetrahydrofuran, cooled in an ice bath, is added 125 ml. of 1 M borane in tetrahydrofuran, dropwise over 10 minutes. The mixture is stirred at room temperature for one hour, refluxed for 6 hours and then stirred at room temperature for 16 hours. The reaction is decomposed by the addition of 50 ml. of 6 N hydrochloric acid and then 75 ml. of 5 N sodium hydroxide is added. Most of the solvent is evaporated, the residue is extracted with methylene chloride and the extract is evaporated to an oil. This oil is dissolved in hot hexane, filtered through diatomaceous earth and evaporated to an oil which crystallizes giving the desired product as colorless crystals, mp. 53°-56° C.

Workup

  1. additionis added 125 ml
  2. temperaturerefluxed for 6 hours
  3. stirringstirred at room temperature for 16 hours
  4. additionThe reaction is decomposed by the addition of 50 ml
  5. customMost of the solvent is evaporated
  6. extractionthe residue is extracted with methylene chloride
  7. customthe extract is evaporated to an oil
  8. dissolutionThis oil is dissolved in hot hexane
  9. filtrationfiltered through diatomaceous earth
  10. customevaporated to an oil which
  11. customcrystallizes

Sources & evidence

ORD record
ord-7278a1d60cb347748ff7a57408baf618
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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