Methylamine → 7-Methylaminosulfonyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride

HRID 6760

Reaction equation

HRID 6760 reaction equation
[CH3:1][NH2:2].C([N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([S:16]([Cl:19])(=[O:18])=[O:17])=[CH:11][CH:12]=2)[CH2:7]1)(=O)C>CO>[ClH:19].[CH3:1][NH:2][S:16]([C:10]1[CH:9]=[C:8]2[C:13]([CH2:14][CH2:15][NH:6][CH2:7]2)=[CH:12][CH:11]=1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 126069042-Acetyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride

Product 1

HCID 220184947-Methylaminosulfonyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methylamine in methanol (2 M, 20 mL) was added to 2-acetyl-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl chloride (2 g). The mixture was stirred at rt for 16 h. Excess methylamine and methanol were evaporated under vacuum and hydrochloric acid (10%, 30 mL) was added to the residue. The mixture was heated at reflux for 3 h and the aqueous solution was evaporated under vacuum. The residue was trituiated with ethyl acetate (2×20 mL) to afford 7-methylaminosulfonyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride (1.9 g).

Workup

  1. customExcess methylamine and methanol were evaporated under vacuum and hydrochloric acid (10%, 30 mL)
  2. additionwas added to the residue
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 3 h
  5. customthe aqueous solution was evaporated under vacuum

Sources & evidence

ORD record
ord-4fa4e9c4bf0048689c33242d888f1867
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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