Hydrochloric Acid → rac-N-[4-(cis-1,2,3a, 4,5,9b-hexahydro-6-hydroxy-3H-benzo[e]indol-3-yl)butyl]phthalimide hydrochloride

HRID 1109175Notes

Reaction equation

HRID 1109175 reaction equation
C[O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:24](=[O:25])[C:23]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]4[C:21]3=[O:30])[C:7]=2[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br.[OH-].[Na+].C(=O)([O-])O.[Na+].[ClH:42]>C(Cl)Cl.C(O)C.O>[ClH:42].[OH:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:21](=[O:30])[C:22]4=[CH:29][CH:28]=[CH:27][CH:26]=[C:23]4[C:24]3=[O:25])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 131718425rac-cis-N-[4-(1,2,3a,4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)butyl]phthalimide

Product 1

HCID 131718426rac-N-[4-(cis-1,2,3a, 4,5,9b-hexahydro-6-hydroxy-3H-benzo[e]indol-3-yl)butyl]phthalimide hydrochlorideYield 14%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.00 g (0.005 mol) of rac-cis-N-[4-(1,2,3a,4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)butyl]phthalimide in 100 ml of methylene chloride was treated dropwise with a solution of 2.4 ml (0.025 mol) of boron tribromide in 100 ml of methylene chloride, whereupon the mixture was stirred at room temperature for 1.5 hours. 32 ml (0.065 mol) of 2N sodium hydroxide solution were added dropwise while cooling with an ice bath. The mixture was poured into water, whereupon an aqueous sodium hydrogen carbonate solution was added until a pH of 8 had been reached. The mixture was extracted with methylene chloride, the extracts were dried over sodium sulphate and the solvent was distilled off in a vacuum. Chromatography over silica gel with methylene chloride/methanol 20:1 yielded an oil which was dissolved in ethanol and treated with ethanolic HCl. Distillation of the solvent and recrystallization from methanol gave 0.3 g (14%) of rac-N-[4-(cis-1,2,3a,4,5,9b-hexahydro-6-hydroxy-3H-benzo[e]indol-3-yl)butyl]phthalimide hydrochloride as white crystals with m.p. 258°-260° (dec.).

Workup

  1. temperaturewhile cooling with an ice bath
  2. additionwas added until a pH of 8
  3. extractionThe mixture was extracted with methylene chloride
  4. dry with materialthe extracts were dried over sodium sulphate
  5. distillationthe solvent was distilled off in a vacuum
  6. customChromatography over silica gel with methylene chloride/methanol 20:1 yielded an oil which
  7. distillationDistillation of the solvent and recrystallization from methanol

Sources & evidence

ORD record
ord-019efbd3099344e6b6d9388ad276b25c
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

Loading…