p-Toluenesulfonic acid → Pyrrolidine, 1-(6-chloro-3,4-dihydro-2-naphthalenyl)-

HRID 569647

Reaction equation

HRID 569647 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 44561396-Chloro-2-tetralone

Product 1

HCID 10444008Pyrrolidine, 1-(6-chloro-3,4-dihydro-2-naphthalenyl)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1155 g (6.4 mol) of 6-chloro-3,4-dihydro-2(1H)-naphthalenone were dissolved in 5 l of toluene, 500 g (7.0 mol) of pyrrolidine and subsequently a solution of 26 g (0.14 mol) of p-toluenesulphonic acid in toluene were added dropwise thereto and the mixture was boiled under reflux. When about 120 ml of water had separated, 4 l of toluene were distilled off and the mixture was left to cool slowly. A solid crystallized out. Filtration and washing with acetone gave 1-(6-chloro-3,4-dihydro-2-naphthyl)pyrrolidine of melting point 117°-118°. Concentration of the mother liquor, suspension of the residue in ether, filtration and washing with acetone gave a further portion of the above product of melting point 117°-118°.

Workup

  1. temperatureunder reflux
  2. customWhen about 120 ml of water had separated
  3. distillation4 l of toluene were distilled off
  4. waitthe mixture was left
  5. temperatureto cool slowly
  6. customA solid crystallized out
  7. filtrationFiltration
  8. washwashing with acetone

Sources & evidence

ORD record
ord-8b2cd8d887db431cba9bbb09b872f1ba
Source dataset
uspto-grants-1988_03
Patent number
US04732979

Linked notes

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