Benzylamine → N-Benzyl-5-hydroxycyclohex-3-enecarboxamide

Reaction equation

[CH:1]12[CH2:9][CH:5]([O:6][C:7]1=[O:8])[CH:4]=[CH:3][CH2:2]2.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([NH:17][C:7]([CH:1]1[CH2:9][CH:5]([OH:6])[CH:4]=[CH:3][CH2:2]1)=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 3767596-Oxabicyclo[3.2.1]oct-3-en-7-one

Product 1

HCID 15064680N-Benzyl-5-hydroxycyclohex-3-enecarboxamide

Procedure

To 6-oxabicyclo[3.2.1]oct-3-en-7-one (2.6 g, 21 mmol) in xylenes (50 ml) under nitrogen was added benzylamine (3.42 g, 32 mmol). The mixture was heated under reflux for 16 h, then cooled to room temperature. The heavy white precipitate was collected by filtration, and recrystallized from dichloromethane/hexane to give the amide as a white solid (3.8 g, 78%, m.p. 127-128(C).

Workup

temperatureThe mixture was heated
temperatureunder reflux for 16 h
filtrationThe heavy white precipitate was collected by filtration
customrecrystallized from dichloromethane/hexane

Sources & evidence

ORD record: ord-51e232cd75de4882a4c8b9cf54da932f
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402592B2

Reaction notes

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