p-Toluenesulfonic acid → HCID 12230452, compound

HRID 1833603Notes

Reaction equation

HRID 1833603 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-toluene sulfonic 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-35b2848df79b464a9addc57ae9ab302e
Source dataset
uspto-grants-1978_01
Patent number
US04066779

Reaction notes

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