Benzenesulfonyl chloride → HCID 44125738, compound

HRID 1444612Notes

Reaction equation

HRID 1444612 reaction equation
[C:1]1([S:7]([Cl:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.[CH2:13]1[C:23]2=[C:24]3[C:19](=[CH:20][CH:21]=[CH:22]2)[CH2:18][CH2:17][N:16]([CH2:25][CH2:26][CH2:27][NH:28][C:29]2[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=2)[CH:15]3[CH2:14]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[ClH:10].[CH2:13]1[C:23]2=[C:24]3[C:19](=[CH:20][CH:21]=[CH:22]2)[CH2:18][CH2:17][N:16]([CH2:25][CH2:26][CH2:27][N:28]([C:29]2[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=2)[S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:15]3[CH2:14]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 23133283HCID 23133283, compound

Product 1

HCID 44125738HCID 44125738, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (48.6 mg, 0.28 mmol) was added to a solution of [3-(2,2a,4,5-Tetrahydro-1H-3-aza-acenaphthylen-3-yl)-propyl]-m-tolyl-amine dihydro-chloride (43.0 mg, 0.11 mmol) and N,N′-diisopropylethylamine (2 ml) in CH2Cl2 (2 mL) and the mixture was stirred overnight at room temperature. The resulting solution was washed with water (3×10 ml), dried over Na2SO4 and evaporated to dryness. The free base was dissolved in ethyl acetate (1 ml). A 2.8 M solution of hydrogen chloride in ethanol (0.10 mL) was then added. The product was crystallized and collected by filtration, and vacuum dried to give a white solid (20.0 mg, 36% yield).

Workup

  1. washThe resulting solution was washed with water (3×10 ml)
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. dissolutionThe free base was dissolved in ethyl acetate (1 ml)
  5. additionA 2.8 M solution of hydrogen chloride in ethanol (0.10 mL) was then added
  6. customThe product was crystallized
  7. filtrationcollected by filtration, and vacuum
  8. customdried

Sources & evidence

ORD record
ord-da2d649c4d854939b68652a57e7ca13f
Source dataset
uspto-grants-2010_02
Patent number
US07662862B2

Reaction notes

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