1-Naphthalenesulfonyl chloride → HCID 86603239, compound

HRID 1930192Notes

Reaction equation

HRID 1930192 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1.C(N(CC)C(C)C)(C)C.[C:27]1([S:37]([Cl:40])(=[O:39])=[O:38])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[ClH:40].[CH2:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][CH2:17][N:8]1[CH2:7][CH2:6][CH2:5][CH2:4][NH:3][S:37]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1)(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 665601-Naphthalenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21994163HCID 21994163, compound

Product 1

HCID 86603239HCID 86603239, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-aminobutyl)-1,2,3,4-tetrahydroisoquinoline dihydrochloride (272 mg, 1 mmol), N,N-diisopropylethylamine (517 mg, 4 mmol) in CH2Cl2 (10 mL), was added naphtalene-1-sulfonyl chloride (238 mg, 1.05 mmol) and was stirred overnight at room temperature. The resulting solution was washed with water (3×15 mL) and dried over Na2SO4, and evaporated to dryness. The free base was dissolved in 2-propanol (5 mL). A 2.8 M solution of hydrogen chloride in ethanol (0.40 mL) was then added. The product was crystallized and collected by filtration, and vacuum dried to give a white solid (310 mg, 72%).

Workup

  1. washThe resulting solution was washed with water (3×15 mL)
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. dissolutionThe free base was dissolved in 2-propanol (5 mL)
  5. additionA 2.8 M solution of hydrogen chloride in ethanol (0.40 mL) was then added
  6. customThe product was crystallized
  7. filtrationcollected by filtration, and vacuum
  8. customdried

Sources & evidence

ORD record
ord-dcc4e43f6a9c47e3a909b9b18a9aa534
Source dataset
uspto-grants-2012_05
Patent number
US08188115B2

Reaction notes

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