Potassium Carbonate → 2-[3-[4-[(4-Chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]propylthio]benzothiazole

HRID 1651554Notes

Reaction equation

HRID 1651554 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.Br[CH2:23][CH2:24][CH2:25][S:26][C:27]1[S:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[O:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:23][CH2:24][CH2:25][S:26][C:27]3[S:28][C:29]4[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=4[N:31]=3)[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 111411972-((4-Chlorophenyl)(4-piperidinyloxy)methyl)pyridineHCID 146721352-(3-Bromopropylthio)benzothiazole

Product 1

HCID 150558602-[3-[4-[(4-Chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]propylthio]benzothiazoleYield 41%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 0.76 g (2.51 mmol) of 4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidine and 0.73 g (2.53 mmol) of 2-(3-bromopropylthio)benzothiazole, were added 6 ml of acetone and 0.35 g (2.53 mmol) of potassium carbonate, and the mixture was stirred at room temperature for 15 hours. After the reaction, the insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography using chloroform alone first, and then a mixture of chloroform and methanol in the volume ratio 30:1 as the eluent, and the desired fraction was concentrated to give 0.52 g (41%) of 2-[3-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]propylthio]benzothiazole as an oil.

Workup

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

Sources & evidence

ORD record
ord-c5c007fb01f84ede8956fc10d5be29ae
Source dataset
uspto-grants-1990_05
Patent number
US04929618

Reaction notes

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