Borane → HCID 68126733, compound

HRID 1580466Notes

Reaction equation

HRID 1580466 reaction equation
[CH3:1][CH:2]1[CH2:22][C:6]2[CH:7]=[CH:8][C:9]3[C:10]4[N:11]([C:12]5[CH:21]=[CH:20][N:19]=[CH:18][C:13]=5[C:14]=4[CH2:15][CH2:16][CH:17]=3)[C:5]=2[CH2:4][CH2:3]1.B>O1CCCC1>[CH3:1][CH:2]1[CH2:22][CH:6]2[CH:7]=[CH:8][C:9]3[C:10]4[N:11]([C:12]5[CH:21]=[CH:20][N:19]=[CH:18][C:13]=5[C:14]=4[CH2:15][CH2:16][CH:17]=3)[CH:5]2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 68127381HCID 68127381, compound

Product 1

HCID 68126733HCID 68126733, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
91 °C

Procedure

A solution of 4.76 g. of 1,2,3,4,8,9-hexahydro-3-methylpyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine (which can be made according to the teachings of U.S. Pat. No. 3,457,271, Column 4, lines 27-54) in 50 ml. of tetrahydrofuran was added dropwise to a stirred 1N-solution of boron hydride in tetrahydrofuran (42 ml.) under a nitrogen blanket. After the addition was complete, the mixture was refluxed under nitrogen for five hours, then cooled in ice and quenched with 20 ml. of 6N hydrochloric acid. The mixture was distilled, the removed liquid being from time to time replaced by addition of dioxane. The mixture was again refluxed at 91°C. for one hour with additional 6N hydrochloric acid, then cooled to 70°C., made basic with sodium hydroxide, and evaporated in vacuum. The semisolid residue was treated with water and chloroform, and the chloroform layer was further worked up to yield 1.50 g. of a solid product, m.p. 128°-131°C. The mother liquors yielded an additional amount of material, m.p. 129.5°-130.5°C. Crystallization from ether raised the melting point to 132°-134°C.; UV spectrum: λmaxCH3OH 279.5 mμ (logε 4.13).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed under nitrogen for five hours
  3. temperaturecooled in ice
  4. customquenched with 20 ml
  5. distillationThe mixture was distilled
  6. additionreplaced by addition of dioxane
  7. temperaturecooled to 70°C.
  8. customevaporated in vacuum
  9. additionThe semisolid residue was treated with water and chloroform
  10. customto yield 1.50 g
  11. customThe mother liquors yielded an additional amount of material, m.p. 129.5°-130.5°C
  12. customCrystallization from ether
  13. temperatureraised the melting point to 132°-134°C.

Sources & evidence

ORD record
ord-544c93ac267f489296796e9880c46402
Source dataset
uspto-grants-1976_01
Patent number
US03932650

Reaction notes

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