Hydrochloric Acid → HCID 21463010, compound

HRID 1940569Notes

Reaction equation

HRID 1940569 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:15]=[C:14]3[C:9]([CH:10]=[CH:11][N:12]=[CH:13]3)=[CH:8][CH:7]=2)=[CH:2]1.Cl.[H][H]>ClCCl.C(O)C.[Pt]=O>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:15]=[C:14]3[C:9]([CH2:10][CH2:11][NH:12][CH2:13]3)=[CH:8][CH:7]=2)=[CH:2]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21462966HCID 21462966, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21463010HCID 21463010, compoundYield 63.5%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(3-thienyl)isoquinoline (0.15 g, 3 mmol) in dichloromethane was treated with an excess of HCl gas. The mixture was evaporated under reduced pressure to give a colourless solid. The solid was dissolved in ethanol, platinum oxide (100 mg) added, the reaction mixture hydrogenated at 50 psi on a Parr apparatus until uptake of hydrogen ceased. The catalyst was collected by filtration and the filtrate was hydrogenated again using fresh catalyst until the starting material had been consumed. The filtrate was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (100 ml), washed with sodium carbonate solution (100 ml), dried over magnesium sulphate, filtered and evaporated under reduced pressure to give crude 7-(3-thienyl)-1,2,3,4-tetrahydroisoquinoline as an oil (0.41 g, 62%). A mixture of this oil (0.40 g, 1.85 mmol) and 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (0.325 g, 1.85 mmol) in toluene (3 ml) was heated at reflux under nitrogen for 6 h. The mixture was allowed to cool and the crystallised product collected. Recrystallisation from toluene afforded the title compound (0.17 g, 28%), m.p. 228°-230° C.; (Found: C, 72.82; H, 5.46; N, 12.05. C21H19N3S requires C, 73.01; H, 5.54; N, 12.16%); δH (DMSO-d6) 2.72 (2H, t, J 5.4 Hz, CH2), 2.80 (2H, t, J 5 Hz, CH2), 3.59 (2H, s, CH2), 3.82 (2H, s, CH2), 7.02 (1H, dd, J 7.7, 4.7 Hz, 5-H), 7.11 (1H, d, J 8.0 Hz, ArH), 7.35 (1H, s, ArH), 7.42-7.50 (3H, m, ArH), 7.57 (1H, dd, J 5.1, 3 Hz, ArH), 7.76 (1H, s, ArH), 8.04 (1H, dd, J 7.7, 1 Hz, 4-H), 8.20 (1H, dd, J 4.6, 1 Hz, 6-H), and 11.49 (1H, br s, NH); m/z (CI+, NH3) 345 (M+1)+.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customto give a colourless solid
  3. filtrationThe catalyst was collected by filtration
  4. customhad been consumed
  5. customThe filtrate was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  7. washwashed with sodium carbonate solution (100 ml)
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a0d761768bc64c5f9a02ac47e6760439
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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