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Potassium Carbonate → HCID 131716391, compound

HRID 1651555
Notes
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Reaction equation

HRID 1651555 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)N2CCNCC2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:21][CH2:22][S:23][C:24]1[S:25][C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=1.O1[CH2:38][CH2:37]OCC1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:14]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:38]2[CH2:37][CH2:24][N:28]([CH2:21][CH2:22][S:23][C:24]3[S:25][C:26]4[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=4[N:28]=3)[CH2:27][CH2:26]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 70048BenzhydrylpiperazineHCID 150558582-[(2-Chloroethyl)sulfanyl]-1,3-benzothiazole

Product 1

HCID 131716391HCID 131716391, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a mixture of 1.00 g (3.96 mmol) of 4-(diphenylmethyl)-piperazine and 1.28 g (5.57 mmol) of 2-(2-chloroethylthio)benzothiazole, were added 10 ml of dioxane, 2 ml of dimethylformamide and 0.85 g (6.15 mmol) of potassium carbonate, and the mixture was stirred under reflux for 3 hours. After the reaction, the insolubles were filtered off, and the filtrate was concentrated. The residue was separated by silica gel column chromatography using a mixture of chloroform and methanol in the volume ratio 30:1 as the developing solvent, and the desired fraction was concentrated under reduced pressure to give 0.61 g (35%) of 2-[2-[4-(diphenylmethyl)-1-piperadinyl]-ethylthio]benzothiazole as an oil.

Workup

  1. temperatureunder reflux for 3 hours
  2. customAfter the reaction
  3. filtrationthe insolubles were filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was separated by silica gel column chromatography
  6. additiona mixture of chloroform and methanol in the volume ratio 30:1 as the developing solvent
  7. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-be12788ba41d40889f3f284a10adc7b2
Source dataset
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04929618

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes