Phenethylamine → HCID 14071374, compound

HRID 1708837Notes

Reaction equation

HRID 1708837 reaction equation
[CH3:1][C:2]1O[C:4]([CH3:19])=[C:5]([CH3:18])[C:6](=[O:17])[C:7]=1[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9].[CH:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][NH2:28])=[CH:22][CH:21]=1.C1(C)C=CC=CC=1.[OH-].[Na+]>CO.CCOCC.O>[CH3:1][C:2]1[N:28]([CH2:27][CH2:26][C:23]2[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=2)[C:4]([CH3:19])=[C:5]([CH3:18])[C:6](=[O:17])[C:7]=1[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9]

Participants

8

Reactant 4

HCID 1001PhenethylamineHCID 1140TolueneHCID 14798Sodium HydroxideHCID 140713732,5,6-Trimethyl-4-oxo-N-phenyl-4H-pyran-3-carboxamide

Product 1

HCID 14071374HCID 14071374, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 1 g (3.89 mmol) of 2,5,6-trimethyl -4-oxo-N-phenyl-4H-pyran-3-carboxamide, 0.71 g (5.83 mmol) of β-phenethylamine and 5 ml of toluene, 0.4 ml of 1N solution of sodium hydroxide in methanol were added and stirred overnight at room temperature. After addition of about 10 ml of water and about 10 ml of ether, the mixture was shaken and allowed to stand. The crystals precipitated were separated by filtration and dried in vacuo to afford 1.16 g of the title compound having m.p. 191°-193° C.

Workup

  1. additionwere added
  2. stirringthe mixture was shaken
  3. customThe crystals precipitated
  4. customwere separated by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-68f04a2fb2bd449bb495f0afede7410c
Source dataset
uspto-grants-1990_08
Patent number
US04946497

Reaction notes

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