Dichloromethane → HCID 4738810, compound

HRID 1481883Notes

Reaction equation

HRID 1481883 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[CH3:21])[CH2:10][CH2:9]1)=O)(C)(C)C.ClCCl.FC(F)(F)C(O)=O>>[F:20][C:18]1[CH:17]=[CH:16][C:15]([CH3:21])=[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 89692897HCID 89692897, compound

Product 1

HCID 4738810HCID 4738810, compoundYield 118.8%

Procedure

In a 20 ml scintillation vial equipped with a magnetic stir bar and fitted with a nitrogen inlet, the 4-(5-fluoro-2-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester 16c (203.70 mg, 0.69 mmol) was taken up in clean, dry, reagent grade dichloromethane (5.00 ml, 77.53 mmol). The mixture was stirred until all solids were in solution and the trifluoroacetic acid (0.50 ml, 6.73 mmol) was added in one portion. The reaction stirred at room temperature for 1 h. After 1 h, the volatiles were removed under reduced pressure. The yellow oil was then taken back up in 5 ml of dichloromethane and the volatiles were removed once more under reduced pressure. The resultant yellow oil was further dried under high vacuum. The product, 1-(5-fluoro-2-methyl-phenyl)-piperazine 16d (160.10 mg, 0.82 mmol), was isolated as a yellow oil and was carried on without further purification.

Workup

  1. customIn a 20 ml scintillation vial equipped with a magnetic stir bar
  2. customfitted with a nitrogen inlet
  3. customdry
  4. stirringThe reaction stirred at room temperature for 1 h
  5. customthe volatiles were removed under reduced pressure
  6. customthe volatiles were removed once more under reduced pressure
  7. customThe resultant yellow oil was further dried under high vacuum

Sources & evidence

ORD record
ord-f193a976512043f6a94e61974bba2519
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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