Norfenefrine → 3-(2-{1-[4-(1,1-Dimethyl-propyl)-benzenesulfonyl]-piperidin-4-ylamino}-1-hydroxy-ethyl)-phenol

HRID 479966Notes

Reaction equation

[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][CH3:4].[CH:22]1[CH:27]=[C:26]([OH:28])[CH:25]=[C:24]([CH:29]([OH:32])[CH2:30][NH2:31])[CH:23]=1>>[CH3:1][C:2]([C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]2[CH2:16][CH2:17][CH:18]([NH:31][CH2:30][CH:29]([C:24]3[CH:25]=[C:26]([OH:28])[CH:27]=[CH:22][CH:23]=3)[OH:32])[CH2:19][CH2:20]2)(=[O:13])=[O:14])=[CH:10][CH:11]=1)([CH3:5])[CH2:3][CH3:4]

Participants

Reactant 2

HCID 4538Norfenefrine

HCID 699516124-(1,1-Dimethyl-propyl)-benzenesulfonyl-piperidin-4-one

Product 1

HCID 699529903-(2-{1-[4-(1,1-Dimethyl-propyl)-benzenesulfonyl]-piperidin-4-ylamino}-1-hydroxy-ethyl)-phenol

Procedure

The title compound was prepared from 4-(1,1-dimethyl-propyl)-benzenesulfonyl-piperidin-4-one and norphenylephrine according to the reductive amination procedure of Intermediate 21 as an off-white solid; 1H NMR (DMSO) δ 0.60 (t, J=7.32 Hz, 3H), 1.28 (s, 6H), 1.60-1.68 (m, 2H), 1.77-1.91 (m, 2H), 2.27-2.45 (m, 4H), 2.51-2.56 (m, 2H), 2.56-2.59 (m, 2H), 3.42-3.47 (m, 2H), 4.42-4.44 (m, 2H), 5.18 (bs, 1H), 6.57-6.60 (m, 1H), 6.67-6.71 (m, 2H), 7.05 (t, J=7.74 Hz, 1H), 7.58 (d, J=8.61 Hz, 2H), 7.65 (d, J=8.58 Hz, 2H) 9.25 (s, 1H); MS (ES) m/z 446.9 (MH+); HRMS for C24H34N2O4S: 447.2323

Sources & evidence

ORD record: ord-5ef9845ba2ce4fd7ac50e4b93f4293d8
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649603B2

Reaction notes

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