2-(Dimethylamino)ethanol → 4-benzyloxy-1-{4-[2-(dimethylamino)ethoxy]phenyl}-1H-pyridin-2-one

HRID 15033

Reaction equation

HRID 15033 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:11](=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])=[CH:19][CH:20]=2)[C:11](=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 684312834-benzyloxy-1-(4-hydroxyphenyl)-1H-pyridin-2-one

Product 1

HCID 115596254-benzyloxy-1-{4-[2-(dimethylamino)ethoxy]phenyl}-1H-pyridin-2-oneYield 66.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Benzyloxy-1-(4-hydroxyphenyl)-1H-pyridin-2-one (150 mg, 0.511 mmol), 2-(dimethylamino)ethanol (0.057 mL, 0.562 mmol), triphenylphosphine (269 mg, 1.02 mmols) and diethyl azodicarboxylate (0.163 mL, 1.02 mmols) were stirred overnight in THF (4 mL). Concentrating the reaction liquid under reduced pressure, the resulting residue was purified on silica gel column chromatography (C-300, methanol: chloroform=1:20-1:10) to provide the title compound (124 mg, 60%).

Workup

  1. concentrationConcentrating
  2. customthe reaction liquid under reduced pressure
  3. customthe resulting residue was purified on silica gel column chromatography (C-300, methanol: chloroform=1:20-1:10)

Sources & evidence

ORD record
ord-03e023041a31460a9e95a92d281c2f32
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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