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Dimethylformamide → N-methyl-2-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]thiazole-4-carboxamide hydrochloride

HRID 1907386
Notes
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Reaction equation

HRID 1907386 reaction equation
[H-].[Na+].CN(C=O)C.[S:8]1[CH:12]=[CH:11][C:10]2[C:13]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:19][CH2:18]3)=[CH:14][CH:15]=[CH:16][C:9]1=2.[CH3:27][NH:28][C:29]([C:31]1[N:32]=[C:33]([Cl:36])[S:34][CH:35]=1)=[O:30]>O>[ClH:36].[CH3:27][NH:28][C:29]([C:31]1[N:32]=[C:33]([O:26][CH2:25][CH2:24][CH2:23][N:20]2[CH2:19][CH2:18][N:17]([C:13]3[C:10]4[CH:11]=[CH:12][S:8][C:9]=4[CH:16]=[CH:15][CH:14]=3)[CH2:22][CH2:21]2)[S:34][CH:35]=1)=[O:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 53630730N-methyl-2-chlorothiazole-4-carboxamideHCID 574825483-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)propanol

Product 1

HCID 66646049N-methyl-2-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]thiazole-4-carboxamide hydrochlorideYield 75.7%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (55%, oily, 90 mg, 2.2 mmol) was added to a DMF solution (2 ml) of 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propanol (0.2 g, 0.7 mmol) and N-methyl-2-chlorothiazole-4-carboxamide (0.26 g, 1.45 mmol) under ice cooling and the solution was stirred at 80° C. for 1.5 hours. After the reaction solution was cooled to room temperature and water was added thereto, it was extracted with ethyl acetate. The extraction solution with ethyl acetate was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=5:1→ethyl acetate). After the purified product was concentrated under reduced pressure, the residue was dissolved in ethyl acetate. A solution of 4N-hydrochloric acid/ethyl acetate was added to the solution and the insoluble matter precipitated was obtained by filtration and dried to obtain N-methyl-2-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]thiazole-4-carboxamide hydrochloride (0.24 g) as light yellow powder.

Workup

  1. temperatureAfter the reaction solution was cooled to room temperature
  2. extractionit was extracted with ethyl acetate
  3. washThe extraction solution with ethyl acetate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=5:1→ethyl acetate)
  7. concentrationAfter the purified product was concentrated under reduced pressure
  8. dissolutionthe residue was dissolved in ethyl acetate
  9. additionA solution of 4N-hydrochloric acid/ethyl acetate was added to the solution
  10. customthe insoluble matter precipitated
  11. customwas obtained by filtration
  12. customdried

Sources & evidence

ORD record
ord-83f4d8380ff64b468264331276a41011
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598162B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes