Trifluoroacetic acid → (4-Amino-3-fluorophenyl)(piperazin-1-yl)methanone

HRID 1807720Notes

Reaction equation

HRID 1807720 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:23].FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[O:7])=[CH:4][C:3]=1[F:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58055815Tert-butyl 4-(4-amino-3-fluorobenzoyl)piperazine-1-carboxylate

Product 1

HCID 63187976(4-Amino-3-fluorophenyl)(piperazin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-amino-3-fluorobenzoyl)piperazine-1-carboxylate (0.649 mmol, 210 mg) was stirred with dichloromethane (˜2 mL) and trifluoroacetic acid (˜0.5 mL) overnight. The mixture was purified by SCX chromatography to give the intermediate (4-amino-3-fluorophenyl)(piperazin-1-yl)methanone. 2-(4-(Bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.649 mmol, 219 mg), potassium carbonate (0.649 mmol, 90 mg) and acetonitrile (5 mL) were added to the intermediate (4-amino-3-fluorophenyl)(piperazin-1-yl)methanone and the mixture was stirred for 6 hours. The reaction mixture was concentrated under reduced pressure. The residue obtained was stirred in dichloromethane, filtered and the filtrate was purified by silica chromatography (eluting with dichloromethane increasing to ethyl acetate) to afford the title compound (46 mg).

Workup

  1. customThe mixture was purified by SCX chromatography

Sources & evidence

ORD record
ord-1a4b70f9c88d4e0d85cd87c1c02093c0
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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