Hydrochloric Acid → rac-cis-3-(2-cyclopentyl-ethyl)-6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole hydrochloride

HRID 1109121Notes

Reaction equation

HRID 1109121 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:12][C:13]([N:15]2[C@@H:23]3[C@@H:18]([C:19]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:20]=4[CH2:21][CH2:22]3)[CH2:17][CH2:16]2)=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Na+].[ClH:32]>C1COCC1.C(O)C.O.C1COCC1.O>[ClH:32].[CH:7]1([CH2:12][CH2:13][N:15]2[C@@H:23]3[C@@H:18]([C:19]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:20]=4[CH2:21][CH2:22]3)[CH2:17][CH2:16]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131718458rac-cis-3-(cyclopentylacetyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

Product 1

HCID 131718459rac-cis-3-(2-cyclopentyl-ethyl)-6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole hydrochlorideYield 86%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 21881883Oxolane--water (1/1)Solvent

Procedure

1.02 g (0.0269 mol) of lithium aluminum hydride were suspended in 30 ml of THF under argon. A solution of 6.5 g (0.0207 mol) of rac-cis-3-(cyclopentyl-acetyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole in 80 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 1 hour. 10 ml of THF/water 9:1, 2 ml of a 4N aqueous NaOH solution and 2 ml of water were cautiously added dropwise thereto in succession, whereupon the mixture was boiled under reflux for 15 minutes until a complete white precipitate had resulted. After filtration and concentration there was obtained an oil which was dissolved in 100 ml of ethanol. 5.1 ml (0.0245 mol) of 4.78N ethanolic HCl solution were added dropwise thereto, the mixture was stirred for 15 minutes and concentrated. The residue crystallized from 100 ml of hot ethyl acetate. There were obtained 5.87 g (86%) of rac-cis-3-(2-cyclopentyl-ethyl)-6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole hydrochloride as white crystals with m.p. 185°-187° (dec.).

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureunder reflux for 15 minutes until a complete white precipitate
  3. customhad resulted
  4. filtrationAfter filtration
  5. concentrationconcentration there
  6. customwas obtained an oil which
  7. concentrationconcentrated
  8. customThe residue crystallized from 100 ml of hot ethyl acetate

Sources & evidence

ORD record
ord-1a1f52dfb3814d04a645a0eef08440ad
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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