Sodium Iodide → HCID 10046316, compound

HRID 1252068Notes

Reaction equation

HRID 1252068 reaction equation
[C:1]([NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13]Cl)[N:12]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1.C(=O)([O-])O.[Na+].[I-].[Na+]>CN(C)C=O>[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([CH:18]2[CH2:19][CH2:20][N:15]([CH2:13][C:11]3[N:12]=[C:8]([NH:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[S:9][CH:10]=3)[CH2:16][CH2:17]2)=[CH:22]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 11776137HCID 11776137, compound

Product 1

HCID 10046316HCID 10046316, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-pivaloylamino-4-chloromethylthiazole (0.42 g), 3-(4-piperidyl)indole (0.34 g), sodium hydrogen carbonate (0.23 g), N,N-dimethylformamide (4.2 ml) and a trace amount of sodium iodide was stirred at 50° C. for 2 hours. The insoluble material was filtered off and the filtrate was washed with a mixture of chloroform and methanol (10:1 V/V). The washings and the filtrate were combined and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and recrystallized from ethanol to give 4-[4-(3-indolyl)piperidinomethyl]-2-pivaloylaminothiazole (280 mg).

Workup

  1. filtrationThe insoluble material was filtered off
  2. washthe filtrate was washed with a mixture of chloroform and methanol (10:1 V/V)
  3. concentrationconcentrated under reduced pressure
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6d2690ef7e17466bb7562644d3c8ef32
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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