Hydrochloric Acid → trans-2-benzyl-2,3,4,4a,5,9b-hexahydro-5-phenyl-1H-pyrido-[4,3-b]indole Hydrochloride

HRID 27910Notes

Reaction equation

HRID 27910 reaction equation
B.O1CCCC1.[CH2:7]([N:14]1[CH2:32][CH2:31][C:17]2[N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:16]=2[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[ClH:33]>C(O)(=O)C>[ClH:33].[CH2:7]([N:14]1[CH2:32][CH2:31][C@H:17]2[N:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C@@H:16]2[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 8028Tetrahydrofuran3×HCID 130144142-Benzyl-5-phenyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 70573390trans-2-benzyl-2,3,4,4a,5,9b-hexahydro-5-phenyl-1H-pyrido-[4,3-b]indole Hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 0.140 moles of borane in 150 ml. of tetrahydrofuran stirred at 0° C. in a three-necked round bottom flask fitted with magnetic stirrer, thermometer, condenser and addition funnel, and maintained under a nitrogen atmosphere, was added a solution of 23.9 g. (0.071 mole) of 2-benzyl-5-phenyl-1,2,3,4-tetrahydropyrido[4,3-b]indole in 460 ml. of dry tetrahydrofuran. The addition was carried out at such a rate as to maintain the reaction temperature below 9° C. When the addition was completed the resulting mixture was heated to reflux and maintained at this temperature for one hour. The solvent was then evaporated in vacuo to afford a white solid mass which was suspended in 40 ml. of dry tetrahydrofuran and heated, slowly at first, with 180 ml. of a 1:1 by volume mixture of acetic acid and 5 N hydrochloric acid. The resulting suspension was heated at reflux for one hour, then cooled. Evaporation of tetrahydrofuran and part of the acetic acid resulted in precipitation of a white solid which was separated by filtration and washed with water. The solid was resuspended in tetrahydrofuran, filtered, washed with ethyl ether and air dried to afford 16.7 g. (63%) of the desired trans-isomer. M.P. 256°-260° C.

Workup

  1. customfitted with magnetic stirrer
  2. additionthermometer, condenser and addition funnel
  3. temperaturemaintained under a nitrogen atmosphere
  4. additionwas added a solution of 23.9 g
  5. additionThe addition
  6. temperatureto maintain the reaction temperature below 9° C
  7. additionWhen the addition
  8. temperaturewas heated
  9. temperatureto reflux
  10. temperaturemaintained at this temperature for one hour
  11. customThe solvent was then evaporated in vacuo
  12. customto afford a white solid mass which
  13. temperatureThe resulting suspension was heated
  14. temperatureat reflux for one hour
  15. temperaturecooled
  16. customEvaporation of tetrahydrofuran and part of the acetic acid
  17. customresulted in precipitation of a white solid which
  18. customwas separated by filtration
  19. washwashed with water
  20. filtrationfiltered
  21. washwashed with ethyl ether and air
  22. customdried
  23. customto afford 16.7 g

Sources & evidence

ORD record
ord-7ad70165e1ec4e019c2838757ab46ac9
Source dataset
uspto-grants-1980_09
Patent number
US04224329

Reaction notes

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