Acetic Acid → HCID 178500506, compound

HRID 2206548Notes

Reaction equation

HRID 2206548 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH:7]([NH2:9])[CH3:8].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]([C:22](=O)[CH3:23])[C:18]([O:20][CH3:21])=[O:19].C(O)(=O)C>CO>[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH:7](/[N:9]=[C:22](\[CH3:23])/[CH:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[Br:10])[C:18]([O:20][CH3:21])=[O:19])[CH3:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 54499564HCID 54499564, compoundHCID 82306029Methyl 2-(2-bromophenyl)-3-oxobutanoate

Product 1

HCID 178500506HCID 178500506, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(1,4-dioxan-2-yl)ethanamine (2.5 g, 19 mmol) in methanol (100 mL) was added methyl 2-(2-bromophenyl)-3-oxobutanoate (5.4 g, 20 mmol) and acetic acid (1.8 g, 30 mmol). The resulting reaction system was warm to reflux and allowed to stir overnight. The reaction mixture was concentrated and purified by column chromatographed on silica gel (eluted: dichloromethane/methanol 50:1→20:1→5:1) the title compound (1 g, 14%) as a brown solid. LCMS (M+H+) m/z: calcd. 383.07. found 384.9.

Workup

  1. customThe resulting reaction system
  2. temperaturewas warm
  3. temperatureto reflux
  4. concentrationThe reaction mixture was concentrated
  5. custompurified by column
  6. customchromatographed on silica gel (eluted: dichloromethane/methanol 50:1→20:1→5:1) the title compound (1 g, 14%) as a brown solid

Sources & evidence

ORD record
ord-9cf8e57c4e0c419c9c3babe12dfe25d4
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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