2,6-Lutidine → 1-Dodecylazacyclohept-3-ene-2-one

HRID 845102Notes

Reaction equation

HRID 845102 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][CH2:7][CH:8]=[CH: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 141826961-Dodecylazacyclohept-3-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 and 5.1 g (47 mmol) of 2,6-lutidine was refluxed for 3 hours, then cooled to room temperature. 100 ml of toluene was added, the mixture was filtered, and the filtrate was concentrated in vacuo to yield a crude oil. Purification by flash chromatography (silica gel; 7:3 petroleum ether/ether V/V) gave the product as a colorless oil, Rf =0.38; Kuglerohr distilled at 165°-170° C./0.2 mm Hg.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto yield a crude oil
  4. customPurification by flash chromatography (silica gel; 7:3 petroleum ether/ether V/V)

Sources & evidence

ORD record
ord-c9d99cd1c44f401baae3a1b12928968f
Source dataset
uspto-grants-1988_07
Patent number
US04755535

Reaction notes

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