Diisopropylethylamine → HCID 44123941, compound

HRID 1444611Notes

Reaction equation

HRID 1444611 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([Cl:13])(=[O:12])=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.Cl.Cl.[CH2:16]1[C:26]2=[C:27]3[C:22](=[CH:23][CH:24]=[CH:25]2)[CH2:21][CH2:20][N:19]([CH2:28][CH2:29][CH2:30][NH2:31])[CH:18]3[CH2:17]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[ClH:13].[CH2:16]1[C:26]2=[C:27]3[C:22](=[CH:23][CH:24]=[CH:25]2)[CH2:21][CH2:20][N:19]([CH2:28][CH2:29][CH2:30][NH:31][S:10]([C:8]2[CH:7]=[CH:6][C:5]4[O:1][CH2:2][CH2:3][C:4]=4[CH:9]=2)(=[O:12])=[O:11])[CH:18]3[CH2:17]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27761542,3-Dihydrobenzofuran-5-sulfonyl ChlorideHCID 23133278HCID 23133278, compound

Product 1

HCID 44123941HCID 44123941, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Dihydro-benzofuran-5-sulfonyl chloride (24.05 mg, 0.11 mmol) was added to a solution of 3-(2,2a,4,5-Tetrahydro-1H-3-aza-acenaphthylen-3-yl)-propylamine dihydro-chloride (28.92 mg, 0.1 mmol) and N,N′-diisopropylethylamine (51.7 mg, 0.4 mmol) in CH2Cl2 (10 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 (33 mg, 77%).

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-5bb5673c1a6f4f43aa3010a90942a0e3
Source dataset
uspto-grants-2010_02
Patent number
US07662862B2

Reaction notes

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