Water → HCID 131718482, compound

HRID 1109144Notes

Reaction equation

HRID 1109144 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.[N:20]1([CH2:26][CH2:27][NH2:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=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:28]3[CH2:27][CH2:26][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 33944N-(2-Aminoethyl)piperidineHCID 12541369HCID 12541369, compound

Product 1

HCID 131718482HCID 131718482, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

4.0 g (0.01525 mol) of ethyl 1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-naphthylacetate were dissolved in 250 ml of toluene, 4.05 ml (0.0305 mol) of 2-piperidinoethylamine and 0.13 g of p-toluenesulphonic acid monohydrate were added thereto and the mixture was boiled for 4 hours on a water separator. After concentration the residue was hydrogenated with 1.3 g of Raney-nickel in 500 ml of ethanol at 120° and 140 bar for 10 hours. The product was chromatographed over silica gel with CH2Cl2 /MeOH 49:1. There were obtained 4.45 g (89%) of oily rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-(2-piperidinoethyl)-2H-benzo[e]indol-2-one.

Workup

  1. concentrationAfter concentration the residue
  2. customwas hydrogenated with 1.3 g of Raney-nickel in 500 ml of ethanol at 120°
  3. customThe product was chromatographed over silica gel with CH2Cl2 /MeOH 49:1

Sources & evidence

ORD record
ord-91714e1293b2422c8ebb55a624de63cf
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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