2-Phenylethanol → HCID 58494980, compound

HRID 516249Notes

Reaction equation

HRID 516249 reaction equation
Cl[C:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14][C:11]=3[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)=[O:3].[CH2:26]([OH:34])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>N1C=CC=CC=1>[N:4]1([C:2]([O:34][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:3])[C:13]2[C:8](=[CH:9][C:10]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14][C:11]=3[CH:12]=2)[CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 60542-PhenylethanolHCID 58494869HCID 58494869, compound

Product 1

HCID 58494980HCID 58494980, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 200 mg of t-butyl 1-(chlorocarbonyl)-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate in 2 ml of pyridine was added 140 μl of phenethyl alcohol, followed by stirring at 100° C. for 5.5 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 68 mg of 8-t-butyl 1-(2-phenylethyl) 3,4,6,7,9,10-hexahydro-1H-azepino[4,5-g]quinoline-1,8(2H)-dicarboxylate as a yellow viscous substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-de865951b8ae469e8eca5610b437cc86
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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