2-Chlorobenzenesulfonyl chloride → 2-Chloro-N-[4-(7,8-dimethoxy-1-oxo-2,2a,4,5-tetrahydro-1H-3-aza-acenaphthylen-3-yl)-butyl]-benzenesulfonamide hydrochloride

HRID 1988124Notes

Reaction equation

HRID 1988124 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].Cl.Cl.[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:29][CH2:28][C:27]2[C:30]3[CH:20]1[CH2:21][C:22](=[O:35])[C:23]=3[C:24]([O:33][CH3:34])=[C:25]([O:31][CH3:32])[CH:26]=2>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:29][CH2:28][C:27]2[C:30]3[CH:20]1[CH2:21][C:22](=[O:35])[C:23]=3[C:24]([O:33][CH3:34])=[C:25]([O:31][CH3:32])[CH:26]=2)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 673585823-(4-Amino-butyl)-7,8-dimethoxy-2a,3,4,5-tetrahydro-2H-3-aza-acenaphthylen-1-one dihydro-chloride

Product 1

HCID 441239432-Chloro-N-[4-(7,8-dimethoxy-1-oxo-2,2a,4,5-tetrahydro-1H-3-aza-acenaphthylen-3-yl)-butyl]-benzenesulfonamide hydrochlorideYield 119%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chlorobenzenesulfonyl chloride (92.4 mg, 0.44 mmol) was added to a solution of 3-(4-Amino-butyl)-7,8-dimethoxy-2a,3,4,5-tetrahydro-2H-3-aza-acenaphthylen-1-one dihydro-chloride (150 mg, 0.40 mmol) and NN′-diisopropylethylamine (0.400 ml) in CH2Cl2 (20 mL) and the mixture was stirred overnight at room temperature. The resulting solution was washed with water (3×20 mL), dried over Na2SO4 and evaporated to dryness. The free base was dissolved in ethyl acetate (2 ml) and A 2.8 M solution of hydrogen chloride in ethanol was then added. The product was crystallized and collected by filtration, and vacuum dried to give a pale brown solid (135 mg, 66%).

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 ethyl acetate (2 ml)
  5. additionA 2.8 M solution of hydrogen chloride in ethanol was then added
  6. customThe product was crystallized
  7. filtrationcollected by filtration, and vacuum
  8. customdried

Sources & evidence

ORD record
ord-cbf001c4f4e54891a77d2280ca5044cd
Source dataset
uspto-grants-2009_06
Patent number
US07553965B2

Reaction notes

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