3-Amino-1-propanol → [2-(3-Hydroxypropyl)amino-2-oxoethoxy]acetic acid

HRID 1659967Notes

Reaction equation

HRID 1659967 reaction equation
O=C1COCC(=O)N1.CS([O-])(=O)=O.[C:14]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][O:16][CH2:15]1.[NH2:22][CH2:23][CH2:24][CH2:25][OH:26]>>[OH:26][CH2:25][CH2:24][CH2:23][NH:22][C:18](=[O:19])[CH2:17][O:16][CH2:15][C:14]([OH:20])=[O:21]

Participants

5

Reactant 4

HCID 90863-Amino-1-propanolHCID 782321,4-Dioxane-2,6-dioneHCID 85257MethanesulfonateHCID 364836Morpholine-3,5-dione

Product 1

HCID 20558885[2-(3-Hydroxypropyl)amino-2-oxoethoxy]acetic acid

Procedure

4-[2-(4-Bis(2-bromo-p-tolyl)methyl)piperidino)propyl]-3,5-dioxomorpholine.methanesulfonate by (a) reacting diglycolic anhydride and 3-aminopropanol to produce [2-(3-hydroxypropyl)amino-2-oxoethoxy]acetic acid, (b) heating to cyclize the latter to obtain 4-(3-hydroxypropyl)-3,5-dioxomorpholine, (c) esterifying the latter with methanesulfonyl chloride to produce 3-(3,5-dioxomorpholino)propyl methanesulfonate and (d) reacting the mesylate with 4-[bis(2-bromo-p-tolyl)methyl]piperidine.

Sources & evidence

ORD record
ord-0ed6550d63f44eff9c7f10ff723abcf3
Source dataset
uspto-grants-1981_12
Patent number
US04306063

Reaction notes

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