Water → HCID 131718478, compound

HRID 1109140Notes

Reaction equation

HRID 1109140 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=O)[CH:8]2[CH2:13][C:14]([O:16]CC)=O.[NH2:20][CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[CH2:5][CH2:6][C@H:7]3[C@H:8]([CH2:13][C:14](=[O:16])[N:20]3[CH2:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 61055N-(3-Aminopropyl)morpholineHCID 12541369HCID 12541369, compound

Product 1

HCID 131718478HCID 131718478, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.0 g (0.01525 mol) of ethyl 1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-naphthylacetate were dissolved in 80 ml of toluene, 2.22 ml (0.01525 mol) of N-(3-aminopropyl)-morpholine were added thereto and the mixture was boiled for 43 hours on a water separator. After concentration the residue was hydrogenated with 1.5 g of Raney-nickel in 150 ml of ethanol at 120° and 140 bar for 10 hours. The product was chromatographed over silica gel with ethyl acetate/methanol 5:1, dissolved in hot isopropyl ether and crystallized at room temperature. There were obtained 3.58 g (68%) of rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-morpholin-4-yl-propyl)-2H-benzo[e]indol-2-one as white crystals with m.p. 65°-67° and 0.93 g (18%) of oily material from the mother liquors.

Workup

  1. concentrationAfter concentration the residue
  2. customwas hydrogenated with 1.5 g of Raney-nickel in 150 ml of ethanol at 120°
  3. customThe product was chromatographed over silica gel with ethyl acetate/methanol 5:1
  4. dissolutiondissolved in hot isopropyl ether
  5. customcrystallized at room temperature

Sources & evidence

ORD record
ord-7eaded59957c477980f82f515a4c2944
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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