Hydrochloric Acid → HCID 131718456, compound

HRID 1109119Notes

Reaction equation

HRID 1109119 reaction equation
[CH:1]1([CH2:7][CH2:8][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)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:25]([N:27]([CH2:30]C)[CH2:28]C)C.CC(N(C)[Cl:36])=[O:34].Cl>ClCCCl.CN(C)C1C=CN=CC=1.CCOCC.O>[ClH:36].[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][CH2:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:15]=2[CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12663100HCID 12663100, compoundHCID 131718455HCID 131718455, compound

Product 1

HCID 131718456HCID 131718456, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

3.30 g (0.01008 mol) of rac-cis-3-(4-cyclohexyl-butyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol were dissolved in 70 ml of 1,2-dichloroethane. 3.05 g (4.2 ml, 0.0301 mol) of triethylamine and 330 mg (2.70 mmol, 0.27 eq.) of 4-dimethylaminopyridine were added thereto in succession and then 2.8 ml (0.03024 mol) of dimethyl chloroformamide were added dropwise thereto. The mixture was boiled under reflux for 1 hour, then cooled, poured into water and extracted with CH2Cl2. The organic phase was washed with saturated aqueous sodium chloride solution, dried with MgSO4, filtered and concentrated, whereupon the residue was chromatographed over silica gel with n-hexane/ethyl acetate 1:1. The oil obtained (3.2 g) was dissolved in 100 ml of ether. 1.85 ml (8.83 mmol) of 4.78N ethanolic HCl solution were added dropwise thereto and the oily suspension was sonicated for 15 minutes in an ultrasonics bath. Then, it was stirred at room temperature for 1 hour and the separated crystals were filtered off under suction. After recrystallization from 120 ml of hot ethyl acetate and drying at 100°/0.02 Torr for 3 hours there were obtained 2.90 g (83%) of rac-cis-3-(4-cyclohexyl-butyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl dimethylcarbamate hydrochloride as white crystals with m.p. 145°-147°.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturecooled
  3. extractionextracted with CH2Cl2
  4. washThe organic phase was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated, whereupon the residue
  8. customwas chromatographed over silica gel with n-hexane/ethyl acetate 1:1
  9. customThe oil obtained (3.2 g)
  10. customthe oily suspension was sonicated for 15 minutes in an ultrasonics bath
  11. filtrationthe separated crystals were filtered off under suction
  12. customAfter recrystallization from 120 ml of hot ethyl acetate
  13. customdrying at 100°/0.02 Torr for 3 hours there

Sources & evidence

ORD record
ord-f5475b4171324a09b964411010fde321
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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