Water → HCID 131718486, compound

HRID 1109147Notes

Reaction equation

HRID 1109147 reaction equation
Cl.Cl.[N:3]1([CH2:9][CH2:10][N:11]2[C@@H:19]3[C@@H:14]([C:15]4[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[C:16]=4[CH2:17][CH2:18]3)[CH2:13][CH2:12]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:25]([N:27]([CH2:30]C)[CH2:28]C)C.CC(N(C)Cl)=[O:34].O>[OH-].[Na+].C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:25][N:27]([CH3:30])[C:28](=[O:34])[O:24][C:20]1[C:16]2[CH2:17][CH2:18][C@H:19]3[C@H:14]([CH2:13][CH2:12][N:11]3[CH2:10][CH2:9][N:3]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)[C:15]=2[CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12663100HCID 12663100, compoundHCID 131718484HCID 131718484, compound

Product 1

HCID 131718486HCID 131718486, compoundYield 82.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

1.0 g (0.00268 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-(2-piperidinoethyl)-1H-benzo[e]indol-6-ol dihydrochloride was dissolved in a dilute aqueous NaOH solution and extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4, filtered and concentrated. The residue was dissolved in 40 ml of toluene, whereupon 0.28 g (0.39 ml, 0.0279 mol) of triethylamine and 35 mg (0.28 mmol, 0.1 eq.) of 4-dimethylaminopyridine were added in succession and then 0.26 ml (0.0279 mol) of dimethyl chloroformamide was added dropwise. The mixture was boiled under reflux for 2 hours, then cooled, poured into water and extracted with toluene. The organic phase was washed with water, dried with Na2SO4, filtered and concentrated. By chromatography of the residue over silica gel with ethyl acetate/ethanol 1:1 there was obtained 0.82 g (82%) of oily rac-cis-2,3,3a,4,5,9b-hexahydro-3-(2-piperidinoethyl)-1H-benzo[e]indol-6-yl dimethylcarbamate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionwere added in succession
  7. temperatureunder reflux for 2 hours
  8. temperaturecooled
  9. extractionextracted with toluene
  10. washThe organic phase was washed with water
  11. dry with materialdried with Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-0608cabf9b8a4f4ba4bb26289bb669ed
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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