Borane → HCID 86739319, compound

HRID 1903723Notes

Reaction equation

HRID 1903723 reaction equation
B.[Cl:2][N:3]1[CH2:9][C:8]2[CH2:10][CH2:11][CH2:12][CH2:13][C:7]=2[N:6]2[C:14]3[CH:24]=[CH:23][N:22]=[CH:21][C:15]=3[C:16]3[C:17](=O)[CH2:18][CH:19]=[C:4]1[C:5]=32>C1COCC1>[Cl:2][N:3]1[CH2:9][C:8]2[CH2:10][CH2:11][CH2:12][CH2:13][C:7]=2[N:6]2[C:14]3[CH:24]=[CH:23][N:22]=[CH:21][C:15]=3[C:16]3[CH2:17][CH2:18][CH:19]=[C:4]1[C:5]=32

Participants

4

Reactant 2

HCID 6331BoraneHCID 86739320HCID 86739320, compound

Product 1

HCID 86739319HCID 86739319, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane in THF (1 M, 90 ml) was added carefully to a stirred solution-suspension of 6-chloro-1,2,3,4-tetrahydropyrido[4',3':2,3]indolo[1,7-ab][1,4]benzodiazepin-9(8H)-one (Example I-3; 14.4 g) in tetrahydrofuran (200 ml) and the resulting mixture refluxed for 2 hours, cooled and the excess of borane destroyed by dropwise addition of 3 N hydrochloric acid. The mixture was then evaporated to dryness under reduced pressure and the residue refluxed with 3 N hydrochloric acid (200 ml) for 2 hours. Evaporation of the mixture to dryness under reduced pressure provided the salt of the title product which was taken up in a small quantity of water, basified with 10% aqueous sodium hydroxide and extracted thrice with methylene chloride. The combined methylene chloride extracts were washed with water, dried over anhydrous magnesium sulfate and stripped of the solvent under reduced pressure to yield the title product which was recrystallized from a mixture of 2-propanol and methanol, m.p. 210°-212°.

Workup

  1. temperaturethe resulting mixture refluxed for 2 hours
  2. temperaturecooled
  3. customthe excess of borane destroyed by dropwise addition of 3 N hydrochloric acid
  4. customThe mixture was then evaporated to dryness under reduced pressure
  5. temperaturethe residue refluxed with 3 N hydrochloric acid (200 ml) for 2 hours
  6. customEvaporation of the mixture to dryness under reduced pressure

Sources & evidence

ORD record
ord-68d9b863e3564bdb9d317c779a1b79ee
Source dataset
uspto-grants-1984_03
Patent number
US04438120

Reaction notes

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