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1,2-Dichloroethane → 1-(2-Chloroethyl)-4-[4-[4-(6-chloronaphthalene-2-sulfonyl)-2-oxo-1-piperazinylamino]-1-piperidinyl]pyridinium Chloride

HRID 2086290
ノート
印刷プレビュー

反応式

HRID 2086290 の反応式
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:21])[CH:17]=3)[CH:12]=2)(=[O:10])=[O:9])[CH2:4][C:3]1=[O:22].[N:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]2)=[CH:25][CH:24]=1.[Cl:36][CH2:37][CH2:38]Cl.C([BH3-])#N.[Na+]>C(O)C.CO.C(O)(=O)C>[Cl-:21].[Cl:36][CH2:37][CH2:38][N+:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][CH:32]([NH:1][N:2]3[CH2:7][CH2:6][N:5]([S:8]([C:11]4[CH:20]=[CH:19][C:18]5[C:13](=[CH:14][CH:15]=[C:16]([Cl:21])[CH:17]=5)[CH:12]=4)(=[O:9])=[O:10])[CH2:4][C:3]3=[O:22])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 5003444Sodium cyanoborohydrideHCID 113327931-(Pyridin-4-yl)piperidin-4-oneHCID 227270831-Amino-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone

生成物 1

HCID 227271961-(2-Chloroethyl)-4-[4-[4-(6-chloronaphthalene-2-sulfonyl)-2-oxo-1-piperazinylamino]-1-piperidinyl]pyridinium Chloride

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒
HCID 702Ethanol溶媒
HCID 887Methanol溶媒

実験手順

A solution of 1-amino-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (33.98 g) and 1-(4-pyridyl)-4-piperidone (18.50 g) in ethanol (1 L)/1,2-dichloroethane (300 ml) was dehydrated using a Soxlet extractor packed with molecular sieves 4A while refluxing for 3 days. Any insolubles were filtered off and the reaction mixture was concentrated to obtain a residue, which was dissolved in methanol (1 L), combined with acetic acid (33.82 g) while cooling on ice, followed by sodium cyanoborohydride (17.06 g) and then stirred at room temperature for 1 hour. The reaction mixture was concentrated and the residue was dissolved in dichloromethane, washed with aqueous sodium bicarbonate and brine, dried, concentrated and purified by a column chromatography on a silica gel (dichloromethane: methanol=10:1 to dichloromethane: methanol: triethylamine=40:2:1) and a column chromatography on a basic silica gel (tetrahydrofuran to methanol) to obtain the title compound (30 g) as a colorless amorphous material.

後処理

  1. temperaturewhile refluxing for 3 days
  2. filtrationAny insolubles were filtered off
  3. concentrationthe reaction mixture was concentrated
  4. customto obtain a residue, which
  5. temperaturewhile cooling on ice
  6. concentrationThe reaction mixture was concentrated
  7. dissolutionthe residue was dissolved in dichloromethane
  8. washwashed with aqueous sodium bicarbonate and brine
  9. customdried
  10. concentrationconcentrated
  11. custompurified by a column chromatography on a silica gel (dichloromethane: methanol=10:1 to dichloromethane: methanol: triethylamine=40:2:1)

出典と根拠

ORDレコード
ord-339442a0c7634b65911f992812c5ac59
出典データセット
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06723722B1

反応ノート

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