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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
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HRID 2086290 반응식
[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
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참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매
HCID 702Ethanol용매
HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-339442a0c7634b65911f992812c5ac59
출처 데이터셋
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06723722B1

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