Hydrochloric Acid → HCID 131718430, compound

HRID 1109101Notes

Reaction equation

HRID 1109101 reaction equation
[ClH:1].C[O:3][C:4]1[C:16]2[CH2:15][CH2:14][C@H:13]3[C@H:9]([CH2:10][CH2:11][N:12]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]3[C:27](=[O:28])[C:26]4=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]4[C:24]3=[O:33])[C:8]=2[CH:7]=[CH:6][CH:5]=1.B(Br)(Br)Br.[OH-].[Na+].C(=O)([O-])O.[Na+].Cl>C(Cl)Cl.C(O)C.O>[ClH:1].[OH:3][C:4]1[C:16]2[CH2:15][CH2:14][C@H:13]3[C@H:9]([CH2:10][CH2:11][N:12]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]3[C:24](=[O:33])[C:25]4=[CH:32][CH:31]=[CH:30][CH:29]=[C:26]4[C:27]3=[O:28])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 131718432HCID 131718432, compound

Product 1

HCID 131718430HCID 131718430, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.80 g (0.004 mol) of rac-cis-N-[6-(1,2,3a,4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)hexyl]phthalimide hydrochloride in 100 ml of methylene chloride was treated dropwise with a solution of 1.8 ml (0.019 mol) of boron tribromide in 10 ml of methylene chloride. The mixture was stirred at room temperature for 1.5 hours, subsequently treated dropwise with 25 ml (0.05 mol) of 2N sodium hydroxide solution while cooling with an ice bath and then poured into water, whereupon aqueous sodium hydrogen carbonate solution was added until a pH of 8 had been reached. The mixture was extracted with chloroform, the extracts were dried over sodium sulphate and the solvent was distilled off in a vacuum. The residue was chromatographed over silica gel with methylene chloride/methanol (20:1). The oil obtained was dissolved in ethanol and treated with ethanolic HCl. Distillation of the solvent and recrystallization from methanol gave 0.93 g (53%) of rac-cis-N-[6-(1,2,3a,4,5,9b-hexa-hydro-6-hydroxy- 3H-benzo[e]indol-3-yl)-hexyl]phthalimide hydrochloride as white crystals with m.p. 218°.

Workup

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

Sources & evidence

ORD record
ord-908a76e7b2a144e59089a4f8fba5b7ec
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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