Triethylamine → HCID 18172460, compound

HRID 397063

Reaction equation

HRID 397063 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[N:8][CH2:7][CH2:6]2.C(N(CC)CC)C.[CH3:26][N:27]1[CH:31]=[C:30]([S:32](Cl)(=[O:34])=[O:33])[N:29]=[CH:28]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH:13]1[CH2:18][CH2:17][N:16]([S:32]([C:30]3[N:29]=[CH:28][N:27]([CH3:26])[CH:31]=3)(=[O:34])=[O:33])[CH2:15][CH2:14]1)=[N:8][CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 181723896-Methoxy-1-piperidin-4-yl-3,4-dihydro-isoquinoline

Product 1

HCID 18172460HCID 18172460, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 6-methoxy-1-piperidin-4-yl-3,4-dihydro-isoquinoline (0.094 g, 0.385 mmol) and triethylamine (0.078 g, 0.77 mmol) in CH2Cl2 (3 ml) was added 1-methyl-1H-imidazole-4-sulfonyl chloride (0.070 g, 0.385 mmol). The reaction mixture was stirred at RT under an atmosphere of N2 overnight. The reaction mixture was diluted with CH2Cl2 (10 ml) and washed with water (2×5 ml). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified via radial chromatography (SiO2, 1 mm, CH2Cl2 to 5% MeOH/CH2Cl2) to give the product as an oil (0.084 g, 0.216 mmol, 56% yield).

Workup

  1. washwashed with water (2×5 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via radial chromatography (SiO2, 1 mm, CH2Cl2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-88f163b020a4417a8afec3291f8f5e4c
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Linked notes

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