Diisopropylethylamine → HCID 11525458, compound

HRID 1348571Notes

Reaction equation

HRID 1348571 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[CH2:11][N:10]([CH2:17][CH2:18][CH2:19][NH2:20])[CH2:9][CH2:8]2.C(N(CC)C(C)C)(C)C.[Cl:30][C:31]1[CH:32]=[C:33]([S:39](Cl)(=[O:41])=[O:40])[C:34]([F:38])=[CH:35][C:36]=1[F:37]>C(Cl)Cl>[Cl:30][C:31]1[C:36]([F:37])=[CH:35][C:34]([F:38])=[C:33]([S:39]([NH:20][CH2:19][CH2:18][CH2:17][N:10]2[CH2:9][CH2:8][C:7]3[C:12](=[CH:13][C:14]([O:15][CH3:16])=[C:5]([O:4][CH3:3])[CH:6]=3)[CH2:11]2)(=[O:41])=[O:40])[CH:32]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27735275-Chloro-2,4-difluorobenzenesulphonyl chlorideHCID 23111955HCID 23111955, compound

Product 1

HCID 11525458HCID 11525458, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-propylamine dihydrochloride (323 mg, 1 mmol), N,N-diisopropylethylamine (517 mg, 4 mmol) in CH2Cl2(15 mL), was added 3-Chloro-4,6-difluorobenzenesulfonyl chloride (259 mg, 1.05 mmol) and was stirred overnight at room temperature. The resulting solution was washed with water (3×20 mL) and dried over Na2SO4, and evaporated to dryness. The free base was dissolved in 2-propanol (5 mL). The product was crystallized in 2-propanol (5 mL) collected by filtration, and vacuum dried to give a white solid (401 mg, 87%).

Workup

  1. washThe resulting solution was washed with water (3×20 mL)
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. dissolutionThe free base was dissolved in 2-propanol (5 mL)
  5. customThe product was crystallized in 2-propanol (5 mL)
  6. filtrationcollected by filtration, and vacuum
  7. customdried

Sources & evidence

ORD record
ord-0b42858fd1174b349b6ad7db8808e9e5
Source dataset
uspto-grants-2007_05
Patent number
US07211584B2

Reaction notes

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