p-Toluenesulfonic acid → 1-(6,8-Dichloro-3,4-dihydro-2-naphthyl)pyrrolidine

HRID 569664Notes

Reaction equation

HRID 569664 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH:8]=[C:7]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 36539736,8-Dichloro-2-tetralone

Product 1

HCID 221654551-(6,8-Dichloro-3,4-dihydro-2-naphthyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

30.0 g of 6.8-dichloro-3,4-dihydro-2(1H)-naphthalenone were boiled at reflux for 2 hours in 250 ml of benzene and 11.5 ml of pyrrolidine in the presence of 0.5 g of anhydrous p-toluenesulphonic acid. For purification, the 1-(6,8-dichloro-3,4-dihydro-2-naphthyl)pyrrolidine obtained was triturated with 150 ml of isopropyl ether. The filtered-off solid exhibits a melting point of 84°-86°. A further portion of melting point 84.5°-85.5° can be isolated from the mother liquors. The two portions were combined and, after recrystallization from isopropyl ether, there was obtained 1-(6,8-dichloro-3,4-dihydro-2-naphthyl)pyrrolidine of melting point 85.5°-86°.

Workup

  1. customFor purification

Sources & evidence

ORD record
ord-276a400cb66a421e846629487ca225a2
Source dataset
uspto-grants-1988_03
Patent number
US04732979

Reaction notes

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