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

HRID 749112Notes

Reaction equation

HRID 749112 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-carboxamide

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-51e232cd75de4882a4c8b9cf54da932f
Source dataset
uspto-grants-2008_07
Patent number
US07402592B2

Reaction notes

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