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

HRID 725778
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HRID 725778 반응식
[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
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참가 물질

6

반응물 4

HCID 92403-Azabicyclo[3.2.2]nonane2회HCID 81531DiisopropylethylamineHCID 2210045-Chloronaphthalene-1-sulphonyl chlorideHCID 27357775-Chloronaphthalene-2-sulphonyl chloride

생성물 1

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

시약·촉매·용매 1

HCID 6212
Chloroform
용매
2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e870d6ab7355409991e31df3be5bb55b
출처 데이터셋
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05707985

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