3-Azabicyclo[3.2.2]nonane → 3-(5-Chloro-2-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonane

HRID 725778Notes

Reaction equation

HRID 725778 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.[Cl:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15]([S:21](Cl)(=[O:23])=[O:22])=[CH:16]2.C(N(C(C)C)CC)(C)C.ClC1C=CC=C2C=1C=CC=C2S(Cl)(=O)=O>C(Cl)(Cl)Cl>[Cl:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15]([S:21]([N:3]1[CH2:4][CH:5]3[CH2:8][CH2:9][CH:1]([CH2:7][CH2:6]3)[CH2:2]1)(=[O:22])=[O:23])=[CH:16]2

Participants

6

Reactant 4

HCID 92403-Azabicyclo[3.2.2]nonane2×HCID 81531DiisopropylethylamineHCID 2210045-Chloronaphthalene-1-sulphonyl chlorideHCID 27357775-Chloronaphthalene-2-sulphonyl chloride

Product 1

HCID 197087193-(5-Chloro-2-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonane

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The title compound was prepared from the coupling of 3-azabicyclo[3.2.2]nonane and 5-chloro-2-naphthalenesulfonyl chloride. 3-Azabicyclo[3.2.2]nonane (0.31 g, 2.5 mmol) and diisopropyl ethyl amine (1.0 ml, 5.7 mmol) were dissolved in 10 ml chloroform. 5-Chloro-1-naphthalenesulfonyl chloride (0.50 g. 1.9 mmol) in 20 ml chloroform was added dropwise to the solution. After stirring overnight, the solution was washed with saturated sodium bicarbonate solution and brine. Drying over magnesium sulfate and evaporation followed by recrystallization with isopropyl ether/methanol gave 0.50 g (76% yield) of a yellow solid: mp 138°-139° C.; 1H NMR (CDCl3): 8.39 (d, J=8.9, 1 H, H3), 8.33 (d, J=1.7, 1 H, H1), 7.91-7.84 (m, 2 H, H4 and H6), 7.72 (d, J=7.5, 1 H, H8), 7.52 (t, J=7.9, 1 H, H7), 3.31 (d, J=4.2, 4 H, N (CH2R)2), 2.09 (s, 2 H, N(CH2CHR)2), 1.75-1.61 (m, 8 H, alkyl H's); anal calcd for C18H20 2 NO2SCl; C, 61.79; H, 5.76; N, 4.00; found: C, 61.89; H, 5.80; N. 4.08.

Workup

  1. washthe solution was washed with saturated sodium bicarbonate solution and brine
  2. dry with materialDrying over magnesium sulfate and evaporation
  3. customfollowed by recrystallization with isopropyl ether/methanol

Sources & evidence

ORD record
ord-e870d6ab7355409991e31df3be5bb55b
Source dataset
uspto-grants-1998_01
Patent number
US05707985

Reaction notes

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