Phenethylamine → HCID 86714136, compound

HRID 919860Notes

Reaction equation

HRID 919860 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:10][O:11][C:12](=[O:17])[CH2:13][C:14](=O)[CH3:15].[CH3:18][O:19][C:20](=[O:23])[C:21]#[CH:22]>CO>[CH3:18][O:19][C:20](=[O:23])[CH:21]=[CH:22][C:13](=[C:14]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:15])[C:12]([O:11][CH3:10])=[O:17]

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 7757Methyl acetoacetateHCID 13536Methyl propiolate

Product 1

HCID 86714136HCID 86714136, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenethylamine (5.0 mL, 39.7 mmol) was dissolved in MeOH (130 mL). 3-Oxo-butyric acid methyl ester (5.1 mL, 47.6 mmol) was added, and the mixture was refluxed for 3 h. To the reaction mixture was added propynoic acid methyl ester (5.3 mL, 59.5 mmol), and the resulting mixture was then refluxed for 2 days. The solvent was evaporated, and the crude solid was recrystallized from MeOH to give 9.14 g of the title compound as a light orange solid. MS: (+) m/z 326.23 (M+Na).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. temperaturethe resulting mixture was then refluxed for 2 days
  3. customThe solvent was evaporated
  4. customthe crude solid was recrystallized from MeOH

Sources & evidence

ORD record
ord-0e60909154e5420192ceff0f2dfa518b
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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