4-(1-methylpiperidin-4-yloxy)-2-phenylethynyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene → 4-(1-methylpiperidin-4-yloxy)-2-phenethyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

HRID 1773870Notes

Reaction equation

HRID 1773870 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][CH:12]=[C:13]3C#CC2C=CC=CC=2)[CH2:4][CH2:3]1>CO.O=[Pt]=O>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13]3)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 867039564-(1-methylpiperidin-4-yloxy)-2-phenylethynyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

Product 1

HCID 867039574-(1-methylpiperidin-4-yloxy)-2-phenethyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(1-methylpiperidin-4-yloxy)-2-phenylethynyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 34) (50 mg, 0.126 mmole) in MeOH (1.3 mL) is added PtO2 (1.4 mg). The flask is evacuated and filled with hydrogen (balloon). The reaction mixture is stirred at room temperature overnight, then filtered on celite and cake washed with MeOH. Solvent is removed under reduced pressure. The residue is pre-purified by silica gel chromatography using (CH2Cl2:MeOH:NH4OH) as eluent with a gradient from (98:2:0.2) to (95:5:0.5) and the residue is submitted to a preparative thin-layer chromatography eluting with (CH2Cl2:MeOH:NH4OH) (9:1:1) to afford 4-(1-methylpiperidin-4-yloxy)-2-phenethyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene.

Workup

  1. customThe flask is evacuated
  2. additionfilled with hydrogen (balloon)
  3. filtrationfiltered on celite and cake
  4. washwashed with MeOH
  5. customSolvent is removed under reduced pressure
  6. customThe residue is pre-purified by silica gel chromatography
  7. washeluting with (CH2Cl2:MeOH:NH4OH) (9:1:1)

Sources & evidence

ORD record
ord-2b8cb98e5078401a91a8c9a60ed51827
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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