Water → HCID 131718481, compound

HRID 1109143Notes

Reaction equation

HRID 1109143 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][N:10]2[C@@H:18]3[C@@H:13]([C:14]4[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[C:15]=4[CH2:16][CH2:17]3)[CH2:12][CH2:11]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:24]([N:26]([CH2:29]C)[CH2:27]C)C.CC(N(C)Cl)=[O:33].O>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:24][N:26]([CH3:29])[C:27](=[O:33])[O:23][C:19]1[C:15]2[CH2:16][CH2:17][C@H:18]3[C@H:13]([CH2:12][CH2:11][N:10]3[CH2:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[C:14]=2[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12663100HCID 12663100, compoundHCID 131718480HCID 131718480, compound

Product 1

HCID 131718481HCID 131718481, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

3.37 g (0.01065 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-(3-morpholin-4-yl-propyl)-1H-benzo[e]indol-6-ol were dissolved in 60 ml of toluene. 2.155 g (2.97 ml, 0.0214 mol) of triethyl-amine and 130 mg (1065 mmol, 0.1 eq.) of 4-dimethylaminopyridine were added thereto in succession and then 1.96 ml (0.0213 mol) of dimethyl chloroformamide were added dropwise thereto. 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 methanol there were obtained 3.66 g (89%) of oily rac-cis-2,3,3a,4,5,9b-hexahydro-3-(3-morpholin-4-yl-propyl)-1H-benzo[e]indol-6-yl dimethylcarbamate.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperaturecooled
  3. extractionextracted with toluene
  4. washThe organic phase was washed with water
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3a162ef218cc4b04b116e2fbf769ff46
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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