N-Methylethylamine → 6-(Ethyl-methyl-amino)-3,4-dihydro-2H-isoquinolin-1-one

HRID 2069763Notes

Reaction equation

HRID 2069763 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.[CH2:13]([NH:15][CH3:16])[CH3:14]>>[CH2:13]([N:15]([CH3:16])[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2)[CH3:14]

Participants

3

Reactant 2

HCID 12219N-MethylethylamineHCID 107257096-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 592163926-(Ethyl-methyl-amino)-3,4-dihydro-2H-isoquinolin-1-oneYield 85.1%

Conditions

Temperature
150 °C

Procedure

6-Fluoro-3,4-dihydro-2H-isoquinolin-1-one (2.00 g, 12.1 mmol) was deposited in a sealed tube with N-ethylmethylamine (4.0 mL, 47 mmol). This was heated at 150° C. for 24 hours. This was concentrated in vacuo and purified by flash chromatography (elution with ethylacetate) to yield 6-(Ethyl-methyl-amino)-3,4-dihydro-2H-isoquinolin-1-one (2.10 g, 10.3 mmol). MS (ESI) 205.1 (M+H)+.

Workup

  1. concentrationThis was concentrated in vacuo
  2. custompurified by flash chromatography (elution with ethylacetate)

Sources & evidence

ORD record
ord-49cd25d163dc4f409e354bfd306914a6
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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