2,6-Lutidine → 1-Dodecylazacyclohept-4-ene-2-one

HRID 845103Notes

Reaction equation

HRID 845103 reaction equation
Br[CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:3]1=[O:21].N1C(C)=CC=CC=1C>C1(C)C=CC=CC=1>[CH2:9]([N:4]1[CH2:5][CH2:6][CH:7]=[CH:8][CH2:2][C:3]1=[O:21])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 79372,6-LutidineHCID 141826953-Bromo-1-dodecylazacycloheptan-2-one

Product 1

HCID 141826971-Dodecylazacyclohept-4-ene-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 10.0 g (28 mmol) of 3-bromo-1-dodecylazacycloheptan-2-one (Example 1-A) and 5.1 g 47 mmol) of 2,6-lutidine was refluxed for 3 hours. The reaction was cooled to room temperature, 100 ml of toluene was added, and the mixture was filtered. The filtrate was concentrated in vacuo and the residue subjected to flash chromatography (silica gel, 7:3 petroleum ether/EtOAc V/V) to yield the product as a white solid, Rf =0.5; Kuglerohr distilled at 155°-160° C./0.2 mm Hg.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1e800c1e136a47a8963aa45df5ee5891
Source dataset
uspto-grants-1988_07
Patent number
US04755535

Reaction notes

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