p-Toluenesulfonic acid → HCID 12230452, compound

HRID 441612Notes

Reaction equation

HRID 441612 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][CH:8]=[C:7]([CH2:10][CH2:11][OH:12])[C:5]=2[CH:6]=1.[Cl:13][CH2:14][CH2:15][CH2:16][C:17](=O)[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:13][CH2:14][CH2:15][CH2:16][C:17]1([CH3:18])[C:8]2[NH:9][C:4]3[C:5]([C:7]=2[CH2:10][CH2:11][O:12]1)=[CH:6][CH:1]=[CH:2][CH:3]=3

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 10685TryptopholHCID 799932-Pentanone, 5-chloro-

Product 1

HCID 12230452HCID 12230452, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of tryptophol (15 g, 0.09 M) in 150 ml of benzene, 5-chloro-2-pentanone (12 g, 0.10 M) is added. The mixture is heated in the presence of 200 mg of p-toluenesulfonic acid and hydrated alkali-aluminum silicate (Molecular Sieves No. 4). After 1 hr. of refluxing, 400 mg more of acid is added. After a total of 2 hr. the reaction is cooled, filtered and washed with 5% sodium bicarbonate, water and dried over sodium sulfate. Evaporation under reduced pressure affords an oil. This oil is purified by chromatography on silica gel. Elution with benzene and concentration of the eluent gives 1-(3-chloropropyl)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole, nmr (CDCl3) δ1.33 (3H); 1.93 (4H), 2.75 (2H).

Workup

  1. temperatureof refluxing
  2. addition400 mg more of acid is added
  3. customAfter a total of 2 hr
  4. temperaturethe reaction is cooled
  5. filtrationfiltered
  6. washwashed with 5% sodium bicarbonate, water
  7. dry with materialdried over sodium sulfate
  8. customEvaporation under reduced pressure
  9. customaffords an oil
  10. customThis oil is purified by chromatography on silica gel
  11. washElution with benzene and concentration of the eluent

Sources & evidence

ORD record
ord-e4f1a9121d4543c2900bbe6f325ab262
Source dataset
uspto-grants-1977_08
Patent number
US04041169

Reaction notes

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