Hydrochloric Acid → N-(1,2,3,4-tetrahydroisoquinolin-5-yl)methanesulfonamide hydrochloride

HRID 1003995Notes

Reaction equation

HRID 1003995 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[CH:11]2)(=[O:4])=[O:3].[ClH:16]>C(O)C.[Pt](=O)=O>[ClH:16].[CH3:1][S:2]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][NH:10][CH2:11]2)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 187652015-Methanesulfonamidoisoquinoline

Product 1

HCID 22218092N-(1,2,3,4-tetrahydroisoquinolin-5-yl)methanesulfonamide hydrochloride

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-methanesulfonamidoisoquinoline (3.50 g, 0.0156 mol) in ethanol (250 ml) was treated with platinum dioxide (1.5 g) and 1N aqueous hydrochloric acid (15.7 ml). The mixture was hydrogenated at a pressure of 414 kPa (60 psi) for 16 hours, after which time the reaction mixture was filtered. The filtrate was evaporated under reduced pressure and triturated with dichloromethane to afford the subtitle compound as a colourless solid. The solid residue from the filtration was taken up into methanol:water (1:2, v/v), and the suspension filtered, washing with dichloromethane (3×). This filtrate was evaporated to afford a second crop of the subtitle compound (total yield 3.45 g, 84%). Rf 0.21 (0.880 aqueous ammonia:methanol:dichloromethane, 1:10:90, v/v). 1H NMR (D6 -DMSO) δ: 2.96-3.10 (2H, m), 3.31 (3H, m), 4.21 (2H, s), 7.12 (1H, m), 7.26 (2H, m), 9.24 (1H, s), 9.61 (2H, bs).

Workup

  1. filtrationafter which time the reaction mixture was filtered
  2. customThe filtrate was evaporated under reduced pressure
  3. customtriturated with dichloromethane

Sources & evidence

ORD record
ord-2cd108771b1541f29b0e39fef03f160a
Source dataset
uspto-grants-2000_04
Patent number
US06048864

Reaction notes

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