Sodium Hydroxide → 4-Benzyl-N-hydroxymorpholine-2-carboximidamide

HRID 1750306Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]#[N:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:17][OH:18].[OH-].[Na+]>>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14](=[N:17][OH:18])[NH2:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 443297Hydroxyamine hydrochloride

HCID 156511954-Benzylmorpholine-2-carbonitrile

Product 1

HCID 748942584-Benzyl-N-hydroxymorpholine-2-carboximidamide

Procedure

Reaction of 4-benzylmorpholine-2-carbonitrile with hydroxylamine hydrochloride and sodium hydroxide provided 4-benzyl-N′-hydroxymorpholine-2-carboximidamide, which was condensed with cyclopropanecarboxylic acid using 1,3-dicyclohexylcarbodiimide. Cyclization using tetrabutylammonium fluoride (see A. R. Gangloff et al., Tetrahedron Lett. 2001, 42, 1441-1443), followed by debenzylation, afforded 2-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)morpholine.

Sources & evidence

ORD record: ord-721d35e5b6ea4d8ab144be1d23031f8b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156845B2

Reaction notes

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