Isopropanol → N-benzyl-N-(2-hydroxyoctyl)hydroxylamine

HRID 579816Notes

Reaction equation

[CH2:1]([NH:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]/[CH:17]=[O:18].[CH:19](O)(C)C>>[CH2:1]([N:8]([CH2:19][CH:17]([OH:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 3776Isopropanol

HCID 2794173Benzylhydroxylamine

HCID 5283324(E)-2-Octenal

Product 1

HCID 14646909N-benzyl-N-(2-hydroxyoctyl)hydroxylamineYield 38%

Procedure

The procedure of Example 1 is repeated using 5.0 g of N-benzylhydroxylamine and 5.26 g octene-1-oxide in 20 ml of isopropanol. Purification by liquid chromatography affords the title compound in a 38% yield as a colorless oil.

Workup

customPurification by liquid chromatography

Sources & evidence

ORD record: ord-8bab0d56ee39490da83c43e40367ca53
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04749733

Reaction notes

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