2-Chlorobenzenesulfonyl chloride → HCID 67099968, compound

HRID 2077030Notes

Reaction equation

HRID 2077030 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].[ClH:12].Cl.[NH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][N:21]2[CH2:30][CH2:29][C:28]3[C:23](=[CH:24][C:25]([O:33][CH3:34])=[C:26]([O:31][CH3:32])[CH:27]=3)[CH2:22]2)[CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:12])=[CH:4][C:3]=1[S:8]([N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][N:21]2[CH2:30][CH2:29][C:28]3[C:23](=[CH:24][C:25]([O:33][CH3:34])=[C:26]([O:31][CH3:32])[CH:27]=3)[CH2:22]2)[CH2:18][CH2:19]1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67099219HCID 67099219, compound

Product 1

HCID 67099968HCID 67099968, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chlorobenzene-1-sulfonyl chloride (301.9 mg, 1.43 mmol) was added to a solution of 2-(piperidin-4-ylmethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride (472 mg, 1.3 mmol) and N,N-diisopropylethylamine (1.3 ml, 7.5 mmol) in CH2Cl2 (25 mL) and the mixture was stirred overnight at room temperature. The resulting solution was washed with water (3×30 mL), dried over Na2SO4, and evaporated to dryness. The free base was dissolved in ethyl acetate (2 ml). A 2.8 M solution of hydrogen chloride in ethanol (0.6 mL) was then added. The product was crystallized and collected by filtration, and vacuum dried to give a white solid (406 mg, 63%).

Workup

  1. washThe resulting solution was washed with water (3×30 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 (0.6 mL) was then added
  6. customThe product was crystallized
  7. filtrationcollected by filtration, and vacuum
  8. customdried

Sources & evidence

ORD record
ord-99a4212a931f4122835343d6bf09fdd8
Source dataset
uspto-grants-2011_04
Patent number
US07928121B2

Reaction notes

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