Dimethylamine → 5-benzyloxy-2-[2-(N,N-dimethylamino)ethyl]-4-pyridone

HRID 5515Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH2:11][C:12]([CH:15]=[CH2:16])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][NH:19][CH3:20]>C(O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH2:11][C:12]([CH2:15][CH2:16][N:19]([CH3:20])[CH3:18])=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-benzyloxy-2-vinyl-4-pyridone (3.12 g), 50% aqueous solution of dimethylamine (15 ml) and ethanol (35 ml) was heated at 100° C. in a sealed tube for 8 hours. The resulting mixture was cooled and concentrated under reduced pressure to dryness. The residue was triturated with a mixture of ethyl acetate and diisopropyl ether to give 5-benzyloxy-2-[2-(N,N-dimethylamino)ethyl]-4-pyridone (3.45 g) as a powder.

Workup

temperatureThe resulting mixture was cooled
concentrationconcentrated under reduced pressure to dryness
customThe residue was triturated with a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record: ord-7c4e570c849a48728586d884ee0e0858
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05244890

Reaction notes

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