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

HRID 725778
ノート
印刷プレビュー

反応式

HRID 725778 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212
Chloroform
溶媒
2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e870d6ab7355409991e31df3be5bb55b
出典データセット
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05707985

反応ノート

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