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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
Notes
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Reaction equation

HRID 2086290 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-339442a0c7634b65911f992812c5ac59
Source dataset
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06723722B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes