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

HRID 1863157Notes

Reaction equation

HRID 1863157 reaction equation
[C:1]1([CH2:7][C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[NH:14][C:13](=O)[C:12]3=[CH:22][S:23][CH:24]=[C:11]23)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B#B.[ClH:27]>O1CCCC1>[ClH:27].[CH2:8]([N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][CH2:13][C:12]2=[CH:22][S:23][CH:24]=[C:11]12)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 203922494,9-Dihydro-4-phenylacetyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 203922749,10-Dihydro-4-phenethyl-4H-thieno[3,4-b][1,5]benzodiazepine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 6.12 g. portion of 4,9-dihydro-4-phenylacetyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one is suspended in 100 ml. of tetrahydrofuran under argon and stirred with cooling in an ice bath. To this is added 90 ml. of 1 M diborane in tetrahydrofuran over a period of 10 minutes. The mixture is then stirred at room temperature until solution is complete, refluxed for 18 hours, cooled and 45 ml. of 6 N hydrochloric acid is added. The tetrahydrofuran is removed in vacuo and 75 ml. of 5 N sodium hydroxide is added giving the desired final product, mp. 195°-197° C.

Workup

  1. temperaturewith cooling in an ice bath
  2. additionTo this is added 90 ml
  3. temperaturerefluxed for 18 hours
  4. temperaturecooled
  5. customThe tetrahydrofuran is removed in vacuo and 75 ml
  6. additionof 5 N sodium hydroxide is added

Sources & evidence

ORD record
ord-98d8c7a0878c43bea0d5caa2723cd888
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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