Benzylamine → N-Benzyl-5-hydroxycyclohex-3-ene-1-carboxamide

HRID 597963Notes

Reaction equation

HRID 597963 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

3

Reactant 2

HCID 7504BenzylamineHCID 3767596-Oxabicyclo[3.2.1]oct-3-en-7-one

Product 1

HCID 15064680N-Benzyl-5-hydroxycyclohex-3-ene-1-carboxamideYield 78.2%

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

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

Sources & evidence

ORD record
ord-c75270c713304e6cb394d804eee0ba21
Source dataset
uspto-grants-2011_03
Patent number
US07897611B2

Reaction notes

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