4-Toluenesulfonyl chloride → HCID 13749135, compound

HRID 1732052Notes

Reaction equation

HRID 1732052 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[CH2:11][CH2:12][CH2:13][CH:14](O)[C:3]=12.C1(C)C=CC(S([Cl:25])(=O)=O)=CC=1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>N1C=CC=CC=1>[ClH:25].[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[CH2:11][CH2:12][CH2:13][CH:14]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[C:3]=12

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 31268PyrrolidineHCID 13749189HCID 13749189, compound

Product 1

HCID 13749135HCID 13749135, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6,7,8,9-tetrahydro-10-methylpyrido[1,2-a]indol-9-ol (2.01 g, 10 mmol) in dry pyridine (100 mL) was added a solution of p-toluenesulfonyl chloride (7.6 g, 10 mmol) in the same solvent (50 mL) at 5°-10° C. Maintaining this temperature, stirring was continued for 60 minutes, and then, the reaction mixture was treated with distilled pyrrolidine (7.1 g, 100 mmol), and stirred at room temperature for 8 hours. The resultant solution was poured into ice-water, and the product was extracted with methylene chloride. The combined extracts were washed with water, dried (MgSO4), filtered, and evaporated. The residue was chromatographed using methylene chloride/methanol 99:1. The title base 1.8 g (70%) was converted to the hydrochloride salt in acetonitrile with ethereal HCl, and recrystallized from ethanol, m.p. 179°-181° C. (analytical specimen m.p. 182° C.).

Workup

  1. temperatureMaintaining this temperature
  2. stirringstirred at room temperature for 8 hours
  3. extractionthe product was extracted with methylene chloride
  4. washThe combined extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed
  9. customrecrystallized from ethanol, m.p. 179°-181° C. (analytical specimen m.p. 182° C.)

Sources & evidence

ORD record
ord-cb09c0e9fb434c01b756158417d68b7f
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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