p-Toluenesulfonic acid → HCID 20556815, compound

HRID 1660485Notes

Reaction equation

HRID 1660485 reaction equation
CO[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:4]1=[O:13].[C:14]1([CH3:26])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.[C:27]1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:27][O:13][C:4]1[CH:3]=[C:12]2[C:7](=[CH:6][CH:5]=1)[CH2:8][CH:9]([N:23]1[CH2:22][CH2:21][N:20]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH3:26])[CH2:25][CH2:24]1)[CH2:10][CH2:11]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 919652-MeppHCID 14915831HCID 14915831, compound

Product 1

HCID 20556815HCID 20556815, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6 g of methoxy-2-tetralone together with 6 g of N-(o-tolyl)-piperazine are dissolved in 100 ml of toluene whilst warming, 300 mg of p-toluenesulphonic acid are added and the solution refluxed for 24 hours, whereby the water is separated using a Dean-Stark separator. The reaction mixture is then evaporated to dryness, 200 ml of dimethyl formamide and 300 mg of a 10% palladium on charcoal catalyst are added to the obtained 3,4-dihydro-6-methoxy-2-[4-(2-methylphenyl)-1-piperazinyl]-naphthalene, which is hydrogenated at normal pressure. When the take-up of hydrogen ceases the catalyst is filtered off, the solvent evaporated off and the residue chromatographed on Kieselgel with methylene chloride (methanol (99:1). The title compound is obtained as a compact residue. M.P. 286-288° [Hydrochloride salt form].

Workup

  1. temperaturewhilst warming
  2. temperaturethe solution refluxed for 24 hours
  3. customwhereby the water is separated
  4. customThe reaction mixture is then evaporated to dryness, 200 ml of dimethyl formamide and 300 mg of a 10% palladium on charcoal catalyst
  5. additionare added to the obtained 3,4-dihydro-6-methoxy-2-[4-(2-methylphenyl)-1-piperazinyl]-naphthalene, which
  6. filtrationis filtered off
  7. customthe solvent evaporated off
  8. customthe residue chromatographed on Kieselgel with methylene chloride (methanol (99:1)

Sources & evidence

ORD record
ord-d5ec2635def34477ae3a903ae1166128
Source dataset
uspto-grants-1981_12
Patent number
US04308266

Reaction notes

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