Ethanol → 2-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-5-hydroxy-1,2,3,4-tetrahydronaphthalene

HRID 1271296Notes

Reaction equation

HRID 1271296 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C:13]([CH2:19][N:20]([C:22]1[CH:27]=[N:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:24]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:23]=1)[CH3:21])=[CH:14]2)C1C=CC=CC=1.C(O)C>[C].[Pd].C(OCC)(=O)C>[C:28]1([C:25]2[N:26]=[CH:27][C:22]([N:20]([CH2:19][CH:13]3[CH2:12][CH2:11][C:10]4[C:15](=[CH:16][CH:17]=[CH:18][C:9]=4[OH:8])[CH2:14]3)[CH3:21])=[N:23][C:24]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 184526575-(benzyloxy)-2-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-3,4-dihydronaphthalene

Product 1

HCID 184526502-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-5-hydroxy-1,2,3,4-tetrahydronaphthaleneYield 66.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 800 mg of 5-(benzyloxy)-2-{[N-(5,6-diphenylpyrazin-2-yl)-N-methylamino]methyl}-3,4-dihydronaphthalene, 18 ml of ethanol, 15 ml of ethyl acetate and 80 mg of 10% palladium-carbon were added and, after the mixture was hydrogenated under 3 atm at room temperature for 31 hours, the reaction was continued at 30° C. for 23 hours. The catalyst was removed by filtration and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 443 mg of the desired compound as a pale yellow oily substance.

Workup

  1. waitthe reaction was continued at 30° C. for 23 hours
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-65d8fc13221647faa5279be26d6a9529
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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