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Potassium Carbonate → 5-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-1,3,4-thiadiazol-2-amine

HRID 561191
Notes
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Reaction equation

HRID 561191 reaction equation
Cl.[F:2][C:3]([F:18])([F:17])[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[O:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Br[C:20]1[S:24][C:23]([NH2:25])=[N:22][N:21]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:18][C:3]([F:2])([F:17])[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:20]2[S:24][C:23]([NH2:25])=[N:22][N:21]=2)[CH2:9][CH2:8]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 36508832-Amino-5-bromo-1,3,4-thiadiazoleHCID 171780044-(2-(Trifluoromethyl)phenoxy)piperidine hydrochloride

Product 1

HCID 533883675-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-1,3,4-thiadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[2-(trifluoromethyl)phenoxy]piperidine hydrochloride (5.5 g, 2.2 mmol) in DMF (50 mL) was added 5-bromo-1,3,4-thiadiazol-2-amine (3.3 g, 2.2 mmol) and K2CO3 (9.1 g, 6.6 mmol). The reaction was heated at 80° C. with stirring overnight. After cooling, the salt was removed by filtration and the filtrate was evaporated in vacuo. The residue was triturated with EtOAc to afford the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe salt was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was triturated with EtOAc

Sources & evidence

ORD record
ord-2cb4ec98707546dbaad3ef52a0d6935d
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063224B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes