Phenylethanolamine → N-{4-[4-(2-Hydroxy-2-phenyl-ethylamino)-piperidin-1-yl]-phenyl}-4-methoxy-benzenesulfonamide

HRID 1061357Notes

Reaction equation

HRID 1061357 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:26][CH2:27][CH:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[OH:29]>CO.[Pd]>[OH:29][CH:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:27][NH:26][CH:22]1[CH2:23][CH2:24][N:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][S:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)(=[O:10])=[O:11])=[CH:14][CH:15]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 1000PhenylethanolamineHCID 222205564-Methoxy-N-[4-(4-oxo-piperidin-1-yl)-phenyl]benzenesulfonamide

Product 1

HCID 22220320N-{4-[4-(2-Hydroxy-2-phenyl-ethylamino)-piperidin-1-yl]-phenyl}-4-methoxy-benzenesulfonamideYield 61.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-methoxy-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 218) (0.16 g, 0.44 mmol) and 2-amino-1-phenylethanol (0.18 g, 1.3 mmol) in 75 mL of methanol was hydrogenated in the presence of 100 mg of 10% Pd/C under H2 (5˜20 psi) for overnight. The catalyst was then removed by filtering through a short pad of silica gel. The filtrate was concentrated and purified by silica gel chromatography using 5-10% MeOH/CH2Cl2 as eluent to give 0.13 g (61%) of the title compound as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.40 (m, 2H), 1.78-1.92 (m, 2H), 2.50-2.80 (m, 5H), 3.60-3.70 (m, 2H), 3.79 (s, 3H), 4.56-4.60 (m, 1H), 5.26 (brs, 1H), 6.76 (d, J=9.0 Hz, 2H), 6.86 (d, J=9.0 Hz, 2H), 7.04 (d, J=9.0 Hz, 2H), 7.20-7.25 (m, 1H), 7.25-7.36 (m, 4H), 7.58 (d, J=9.0 Hz, 2H); MS (ES) m/z: 482.4 (MH+); HRMS Calcd. for C26H31N3O4S(M+): 481.2035. Found: 481.2028.

Workup

  1. customThe catalyst was then removed
  2. filtrationby filtering through a short pad of silica gel
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-ff5c92d132ae4ecc9a80588758f3d34a
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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