Ethanolamine → 3-Benzyloxy-1-(4'-hydroxybutyl)-2-methylpyrid-4-one

HRID 355285Notes

Reaction equation

HRID 355285 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12]O[C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22].OCCN>>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:17]([CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 258684-Amino-1-butanolHCID 14901193-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 149562933-Benzyloxy-1-(4'-hydroxybutyl)-2-methylpyrid-4-one

Procedure

3-Benzyloxy-2-methyl-4-pyrone, prepared as described under Example 10, is reacted with 1-amino-4-hydroxybutane under substantially similar conditions to those described under Example 11 for reaction with 2-hydroxyethylamine to give 3-benzyloxy-1-(4'-hydroxybutyl)-2-methylpyrid-4-one. This is deprotected using the procedure described under (I) to give 3-hydroxy-1-(4'-hydroxybutyl)-2-methylpyrid-4-one as white crystals, m.p. 126°-128° C.; νmax (nujol) 1630, 3350 cm-1 ; δ(d6DMSO) 1.5 (m, 4H), 2.45 (s, 3H) 3.35 (t. 2H), 4.30 (t, 2H), 7.25 (d 1H), 8.2 (d, 1H).

Sources & evidence

ORD record
ord-9d55e51ba737411a834ee6a0861881b1
Source dataset
uspto-grants-1998_11
Patent number
USRE035948

Reaction notes

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