3,4-dihydro-5-(4-acetonyloxyphenyl) 6-methyl-2(1H)-pyridinone → 5-[4-[2-[(3-Chloro-beta-hydroxyphenethyl)amino]propyloxy]phenyl]-3,4-dihydro-6-methyl-2(1H)-pyridinone

HRID 465429Notes

Reaction equation

HRID 465429 reaction equation
C(=O)(O)O.[OH:5][CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)[CH2:7][NH2:8].[CH2:16]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH2:28][CH2:29][C:30](=[O:34])[NH:31][C:32]=2[CH3:33])=[CH:23][CH:22]=1)[C:17]([CH3:19])=O>>[Cl:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH:6]([OH:5])[CH2:7][NH:8][CH:17]([CH3:19])[CH2:16][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH2:28][CH2:29][C:30](=[O:34])[NH:31][C:32]=2[CH3:33])=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 198745663,4-dihydro-5-(4-acetonyloxyphenyl) 6-methyl-2(1H)-pyridinoneHCID 678659382-(3-Chlorophenyl)-2-hydroxyethylamine carbonate

Product 1

HCID 198745585-[4-[2-[(3-Chloro-beta-hydroxyphenethyl)amino]propyloxy]phenyl]-3,4-dihydro-6-methyl-2(1H)-pyridinone

Procedure

5-[4-[2-[(3-Chloro-β-hydroxyphenethyl)amino]propyloxy]phenyl]-3,4-dihydro-6-methyl-2(1H)-pyridinone was prepared as a 1:1 mixture of diastereoisomers, m.pt. 99°-104° C., from 2-hydroxy-2-(3-chlorophenyl)ethanamine carbonate (0.58 g) and 3,4-dihydro-5-(4-acetonyloxyphenyl) 6-methyl-2(1H)-pyridinone (0.75 g) in an analogous manner to the compound described in Example 38.

Sources & evidence

ORD record
ord-7e6957500bf344dfa2c991ba147d1a83
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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