Norfenefrine → n-(4-{4-[2-Hydroxy-2-(3-hydroxy-phenyl)-ethylamino]-piperidin-1-yl}-phenyl)-4-methoxy-benzenesulfonamide

HRID 1061358Notes

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.[CH:26]1[CH:31]=[C:30]([OH:32])[CH:29]=[C:28]([CH:33]([OH:36])[CH2:34][NH2:35])[CH:27]=1>>[OH:36][CH:33]([C:28]1[CH:27]=[CH:26][CH:31]=[C:30]([OH:32])[CH:29]=1)[CH2:34][NH:35][CH:22]1[CH2:21][CH2:20][N:19]([C:16]2[CH:15]=[CH:14][C:13]([NH:12][S:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)(=[O:10])=[O:11])=[CH:18][CH:17]=2)[CH2:24][CH2:23]1

Participants

Reactant 2

HCID 4538Norfenefrine

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

Product 1

HCID 22220355n-(4-{4-[2-Hydroxy-2-(3-hydroxy-phenyl)-ethylamino]-piperidin-1-yl}-phenyl)-4-methoxy-benzenesulfonamide

Procedure

The title compound was prepared from 4-methoxy-N-[4-(4-oxo-piperidine-1-yl)-phenyl]-benzenesulfonamide (which was obtained in Example 218) and DL-norphenylephrine according to the procedure of Example 255 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.25-1.60 (m, 2H), 2.00-2.15 (m, 2H), 2.50-3.10 (m, 5H), 3.60-3.70 (m, 2H), 3.79 (s, 3H), 4.80-4.90 (m, 1H), 6.05 (brs, 1H), 6.70-6.80 (m, 1H), 6.80-6.85 (m, 4H), 6.90 (d, J=9.0 Hz, 2H), 7.02 (d, J=9.0 Hz, 2H), 7.16 (t, J=7.7 Hz, 1H), 7.60 (d, J=9.0 Hz, 2H), 9.45 (s, 1H), 9.70 (s, 1H); MS (ES) m/z: 498.5 (MH+); HRMS Calcd. for C26H31N3O5S(M+): 497.1984. Found: 497.1961.

Sources & evidence

ORD record: ord-b34d204c96774f31a95b6d56a7d41f85
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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