Trifluoroacetic acid → 1-[[2-Methyl-4-(3-methylphenyl)phenyl]methyl]piperazine

HRID 2278263Notes

Reaction equation

HRID 2278263 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[CH:5]=[CH:4][C:3]=1[CH2:15][N:16]1[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[CH:5]=[CH:4][C:3]=1[CH2:15][N:16]1[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89677194Tert-butyl 4-[[2-methyl-4-(3-methylphenyl)phenyl]methyl]piperazine-1-carboxylate

Product 1

HCID 896771541-[[2-Methyl-4-(3-methylphenyl)phenyl]methyl]piperazineYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100 mL round-bottom flask was charged with tert-butyl 4-[[2-methyl-4-(3-methylphenyl)phenyl]methyl]piperazine-1-carboxylate (2.00 g, 5.26 mmol, 1.00 equiv), trifluoroacetic acid (8 mL), dichloromethane (40 mL). The resulting solution was stirred for 1 h at room temperature and concentrated under reduced pressure to yield 1.50 g (crude) of 1-[[2-methyl-4-(3-methylphenyl)phenyl]methyl]piperazine as light yellow oil. LCMS (ESI, m/z): 281 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91fe3e6cecd74c4285d2f6e7a0644706
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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