Trifluoroacetic acid → (5-Fluoro-2,3-dihydro-benzofuran-2-yl)-piperazin-1-yl-methanone

HRID 1772240Notes

Reaction equation

HRID 1772240 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH:16]2[CH2:20][C:19]3[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:18]=3[O:17]2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[F:25][C:22]1[CH:23]=[CH:24][C:18]2[O:17][CH:16]([C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:15])[CH2:20][C:19]=2[CH:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 901498584-(5-Fluoro-2,3-dihydro-benzofuran-2-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 90149847(5-Fluoro-2,3-dihydro-benzofuran-2-yl)-piperazin-1-yl-methanoneYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 ml round-bottomed flask was added 4-(5-Fluoro-2,3-dihydro-benzofuran-2-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester (1.8 g, 5.1 mmol), 50 ml of dichloromethane, and 2 ml of trifluoroacetic acid. The solution was stirred at room temperature overnight. The solution was made basic with the addition of saturated aqueous sodium bicarbonate. The mixture was then extracted with 4×50 ml of dichloromethane. The organic fractions were combined, dried over magnesium sulfate, filtered, and concentrated under vacuum to afford 1.2 grams of the desired amine as a brown oil (94%).

Workup

  1. extractionThe mixture was then extracted with 4×50 ml of dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8816c05b5b9848649194ca097929fbc6
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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