Potassium Carbonate → N,N-dimethyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide

HRID 984909Notes

Reaction equation

HRID 984909 reaction equation
[CH3:1][N:2]([CH3:22])[S:3]([C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][N:12](C(=O)C(F)(F)F)[CH2:13]2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH3:1][N:2]([CH3:22])[S:3]([C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][NH:12][CH2:13]2)=[CH:8][CH:7]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 571630872-Trifluoroacetyl-1,2,3,4-tetrahydro-isoquinoline-7-sulfonic acid dimethylamide

Product 1

HCID 21393856N,N-dimethyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonamideYield 89%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 2-trifluoroacetyl-1,2,3,4-tetrahydro-isoquinoline-7-sulfonic acid dimethylamide (prepared according to the method of Example 247, Step A, 337 mg, 1.0 mmol) and potassium carbonate (207 mg, 1.5 mmol) in a 3:1 mixture of methanol/water (10 mL) was stirred at room temperature for 1 h and concentrated. The remaining aqueous residue was extracted with 10% isopropanol/chloroform (7×) and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated to give 214 mg (89%) of the title compound of Example 247, Step B as a white solid. 1H NMR (CD3OD, 300 MHz) δ 7.52 (d, 1H), 7.48 (s, 1H), 7.36 (d, 1H), 4.90 (s, 2H), 3.11 (t, 2H), 2.91 (t, 2H), 2.65 (s, 6H); MS (Cl/NH3) 241 (MH+).

Workup

  1. customprepared
  2. concentrationconcentrated
  3. extractionThe remaining aqueous residue was extracted with 10% isopropanol/chloroform (7×)
  4. dry with materialthe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-90ff98b6ceb4424db3b37ee9f11d15c0
Source dataset
uspto-grants-2005_03
Patent number
US06869943B2

Reaction notes

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