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

HRID 596960Notes

Reaction equation

HRID 596960 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. Khun 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 Dean-Stark 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. After 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 γ maxCHCl3 1650 cm-1.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. customWater is collected in a Dean-Stark 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-9256463ed2584977afb33b44ae4d7092
Source dataset
uspto-grants-1977_03
Patent number
US04012511

Reaction notes

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