Ethanolamine → 3-Benzyloxy-1-(5'-hydroxypentyl)-2-methylpyrid-4-one

HRID 355286Notes

Reaction equation

HRID 355286 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][CH2:22][OH:23].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][CH2:22][OH:23])[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 756345-Aminopentan-1-olHCID 14901193-Benzyloxy-2-methyl-4-pyrone

Product 1

HCID 133367163-Benzyloxy-1-(5'-hydroxypentyl)-2-methylpyrid-4-one

Procedure

3-Benzyloxy-2-methyl-4-pyrone, prepared as described under Example 10, is reacted with 1-amino-5-hydroxypentane under substantially similar conditions to those described under Example 11 for reaction with 2-hydroxyethylamine to give 3-benzyloxy-1-(5'-hydroxypentyl)-2-methylpyrid-4-one. This is deprotected using the procedure described under (I) to give 3-hydroxy-1-(5'-hydroxypentyl)-2methylpyrid-4-one as white crystals, m.p. 136°-138° C.; νmax (nujol) 1625, 3350 cm-1 : δ(d6DMSO) 1.3 (m, 6H), 2.40 (s, 3H), 3.25 (t, 2H), 4.20 (t, 2H) 7.20 (d, 1H), 8.15 (d, 1H).

Sources & evidence

ORD record
ord-fae26601df254059897a599da0f75518
Source dataset
uspto-grants-1998_11
Patent number
USRE035948

Reaction notes

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