Acetic Acid → HCID 14155431, compound

HRID 648930Notes

Reaction equation

HRID 648930 reaction equation
[CH3:1][N:2]1[CH2:25][CH2:24][N:5]2[C:6]3[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=3[CH2:8][N:9]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:11]([CH:18]=O)=[C:10]3[CH:4]2[CH2:3]1.B#B.CO.C(O)(=O)C>O1CCCC1>[CH3:1][N:2]1[CH2:25][CH2:24][N:5]2[C:6]3[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=3[CH2:8][N:9]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:11]([CH3:18])=[C:10]3[CH:4]2[CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 6328200DiboronHCID 14155426HCID 14155426, compound

Product 1

HCID 14155431HCID 14155431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.4 g of 1,3,4,16b-tetrahydro-2-methyl-2H,10H-indolo[2,1-c]pyrazino[1,2-a][1,4]benzodiazepine-16-carboxaldehyde in 35 ml tetrahydrofuran is added 17 ml of 1M diborane in tetrahydrofuran. The reaction mixture is heated at reflux temperature for 5 hours. The reaction is then treated with 10 ml methanol and 3.5 ml acetic acid and heating is continued for an additional 1 hour. The solvent is evaporated under reduced pressure and the residue is dissolved in methylene chloride and washed with 5% sodium hydroxide solution. The methylene chloride layer is separated and the solvent evaporated under reduced pressure to yield 1,3,4,16b-tetrahydro-2,16-dimethyl-2H,10H-indolo[2,1-c]pyrazino[1,2-a][1,4]benzodiazepine which is converted to the hydrochloride salt, mp 293°-298° dec.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux temperature for 5 hours
  3. temperatureheating
  4. customThe solvent is evaporated under reduced pressure
  5. dissolutionthe residue is dissolved in methylene chloride
  6. washwashed with 5% sodium hydroxide solution
  7. customThe methylene chloride layer is separated
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-290f8ae2582e4a9aaecb587a1ccbf744
Source dataset
uspto-grants-1988_04
Patent number
US04737496

Reaction notes

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