3-Bromo-1,1,1-trifluoro-2-propanone → HCID 25055180, compound

HRID 1426378Notes

Reaction equation

HRID 1426378 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([NH2:17])=[S:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:19][C:20](=O)[C:21]([F:24])([F:23])[F:22]>C(O)C>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[S:16][CH:19]=[C:20]([C:21]([F:24])([F:23])[F:22])[N:17]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 10848254(1-benzylpiperidin-4-yl)thiourea

Product 1

HCID 25055180HCID 25055180, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (1-benzyl-piperidin-4-yl)-thiourea (0.5 g, 2.0 mmol) (prepared by a procedure similar to that described in WO 03/062215) in ethanol (15 ml) was added 3-bromo-1,1,1-trifluoroacetone (0.22 ml, 2.1 mmol) and the reaction mixture was heated at reflux for 1 h. After evaporation of the solvent, the crude product was crystallized from acetonitrile to yield D8 (0.61 g, 88%) as a white solid. C16H18F3N3S.HBr free base requires 341. Found 342 (MH+).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. customAfter evaporation of the solvent
  4. customthe crude product was crystallized from acetonitrile

Sources & evidence

ORD record
ord-23337ac8f4cd4a5eb3403d8845344b9a
Source dataset
uspto-grants-2015_01
Patent number
US08933101B2

Reaction notes

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