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

HRID 1906181Notes

Reaction equation

HRID 1906181 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.C(OC1C(=O)C=COC=1C)C1C=CC=CC=1.C([N:36]1[CH:41]=[CH:40][C:39](=O)[C:38]([OH:43])=C1C)(=O)C.NCCCCO.OCCN>>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:36]([CH2:41][CH2:40][CH2:39][CH2:38][OH:43])[C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 700EthanolamineHCID 258684-Amino-1-butanolHCID 14901193-Benzyloxy-2-methyl-4-pyroneHCID 867413491-acetyl-3-hydroxy-2-methylpyrid-4-one 3-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 (J), is reacted with 1-amino-4-hydroxybutane under substantially similar conditions to those described under (K) 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.; δmax (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-fbb15af913734b76b45ba7f5e6b6dcc1
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

Loading…