3-Methylindole-1-ethanol → HCID 21389570, compound

HRID 1833558Notes

Reaction equation

HRID 1833558 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][OH:13])[CH:3]=1.O=[C:15]([CH3:23])[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21]>C1C=CC=CC=1>[C:20]([NH:19][CH2:18][CH2:17][CH2:16][C:15]1([CH3:23])[C:3]2=[C:2]([CH3:1])[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]2[CH2:11][CH2:12][O:13]1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 122267423-Methylindole-1-ethanolHCID 21389567HCID 21389567, compound

Product 1

HCID 21389570HCID 21389570, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-methylindole-1-ethanol (4.2 g.) and N-(4-oxopentyl)acetamide (3.7 g), described by L. P. Kuhn et al., J. Am. Chem. Soc., 89, 3858 (1967), in 300 ml of dry benzene is stirred and heated at reflux. Water is collected in a DeanStark trap. After removal of the water five drops of boron trifluoride-etherate is added and the mixture refluxed 30 min. using the water-separator again. Again stirring at room temperature overnight the reaction mixture is evaporated to dryness. The solid residue is dissolved in chloroform and washed successively with 10% aqueous sodium bicarbonate, water, and brine. The chloroform solution is dried over magnesium sulfate, filtered, and evaporated to yield 1-[3-(acetamido)propyl]1,10-dimethyl-3,4-dihydro-1H-1,4-oxazino[4,3-a]indole γmaxCHCl3 1650 cm-1.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. customWater is collected in a DeanStark trap
  4. customAfter removal of the water five drops of boron trifluoride-etherate
  5. additionis added
  6. temperaturethe mixture refluxed 30 min.
  7. customis evaporated to dryness
  8. dissolutionThe solid residue is dissolved in chloroform
  9. washwashed successively with 10% aqueous sodium bicarbonate, water, and brine
  10. dry with materialThe chloroform solution is dried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-773a487bc7bd40cfa3deadea6ce53eaf
Source dataset
uspto-grants-1978_01
Patent number
US04066763

Reaction notes

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