HCID 23353574, compound → HCID 23353564, compound

HRID 235104Notes

Reaction equation

HRID 235104 reaction equation
Br[C:2]1[C:6]([CH2:7][CH2:8][CH3:9])=[CH:5][S:4][C:3]=1[CH:10]1[C:19]2[C:14](=[CH:15][C:16]3[O:22][CH2:21][O:20][C:17]=3[CH:18]=2)[CH2:13][CH2:12][CH:11]1[NH2:23]>C(O)C.[Pd]>[CH2:7]([C:6]1[CH:2]=[C:3]([CH:10]2[C:19]3[C:14](=[CH:15][C:16]4[O:22][CH2:21][O:20][C:17]=4[CH:18]=3)[CH2:13][CH2:12][CH:11]2[NH2:23])[S:4][CH:5]=1)[CH2:8][CH3:9]

Participants

4

Reactant 1

HCID 23353574HCID 23353574, compound

Product 1

HCID 23353564HCID 23353564, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution (0.78 g, 1.96 mmol) of 1-(3-bromo-4-propyl-2-thiophenyl)-1,2,3,4-tetrahydro-6,7-methylenedioxy-2-naphthylamine in ethanol was hydrogenated at 4 Atm H2 with 0.3 g of 10% Pd/C catalyst. The catalyst was removed by filtration, and the flitrate was concentrated to give 0.65 g of the title compound. NMR (CDCl3) δ:6.81 (s, 1H), 6,77 (s, 1H), 6.56 (s, 1H), 6.41 (s, 1H), 5.87 (s, 2H), 3.90 (d, J=8 Hz, 1H), 3.25-3.15 (m, 1H), 2.92-2.78 (m, 2H), 2.54 (t, J=7 Hz, 2H), 2.13-2.05 (m, 1H), 1.8-1.6 (m, 3H), 0.96 (t, J=7 Hz, 3H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe flitrate was concentrated

Sources & evidence

ORD record
ord-f9b05287f3ec42a58c9af7ffce9bc46a
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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