Diisopropylethylamine → 1-{2-[4-(4-Hydroxy-4-methyl-piperidin-1-ylmethyl)-phenyl]-ethyl}-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one

HRID 564112Notes

Reaction equation

HRID 564112 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:13][C:12]2=[O:25])=[CH:5][CH:4]=1.[OH:26][C:27]1([CH3:33])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[OH:26][C:27]1([CH3:33])[CH2:32][CH2:31][N:30]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:13][C:12]3=[O:25])=[CH:5][CH:4]=2)[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 156491744-Methylpiperidin-4-olHCID 670077401-[2-(4-Bromomethyl-phenyl)-ethyl]-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one

Product 1

HCID 580427991-{2-[4-(4-Hydroxy-4-methyl-piperidin-1-ylmethyl)-phenyl]-ethyl}-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 140 mg (0.26 mmol) 1-[2-(4-bromomethyl-phenyl)-ethyl]-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one (example 3.3a) in 1.5 mL DMF is added 61 mg (0.53 mmol) 4-hydroxy-4-methylpiperidine and 0.12 mL (0.66 mmol) N-ethyl-diisopropylamine at RT. The reaction mixture is stirred 2 h at RT and is directly transferred to a reverse HPLC for purification (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Workup

  1. customis directly transferred to a reverse HPLC for purification (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90)

Sources & evidence

ORD record
ord-7649b055d6f34ed8afda14bcdb3993f5
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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