Dimethylamine, hydrochloride → HCID 12742068, compound

HRID 514373Notes

Reaction equation

HRID 514373 reaction equation
O/[CH:2]=[CH:3]/[C:4](=[O:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[CH3:14][NH:15][CH3:16].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH3:14][N:15]([CH3:16])/[CH:2]=[CH:3]/[C:4](=[O:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 12742057HCID 12742057, compound

Product 1

HCID 12742068HCID 12742068, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3E)-4-hydroxy-1-phenylbut-3-en-2-one (1.2 g, 7.4 mmol) in THF (20 mL) was added dimethylamine hydrochloride (1.8 g, 22.2 mmol), K2CO3 (6.1 g, 44.4 mmol) and the mixture was stirred at rt overnight. The mixture was concentrated and purified by flash column chromatography (PE/EtOAc=10:1) to give the title compound (0.6 g, 43%) as a yellow oil. [M+H] Calc'd for C12H15NO, 190. Found, 190.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash column chromatography (PE/EtOAc=10:1)

Sources & evidence

ORD record
ord-de0dac62bed1464ca6719ac69a5831ac
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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