Trifluoroacetic acid → 1-[[4-(2,6-Dimethylpyridin-4-yl)-2-methylphenyl]methyl]piperazine

HRID 2278275Notes

Reaction equation

HRID 2278275 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[C:10]([CH3:28])[CH:9]=2)[CH:5]=[C:4]([CH3:29])[N:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:29][C:4]1[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[C:10]([CH3:28])[CH:9]=2)[CH:7]=[C:2]([CH3:1])[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89677209Tert-butyl 4-[[4-(2,6-dimethylpyridin-4-yl)-2-methylphenyl]methyl]piperazine-1-carboxylate

Product 1

HCID 896769931-[[4-(2,6-Dimethylpyridin-4-yl)-2-methylphenyl]methyl]piperazineYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 50 mL round-bottom flask maintained with an inert atmosphere of nitrogen was charged with tert-butyl 4-[[4-(2,6-dimethylpyridin-4-yl)-2-methylphenyl]methyl]piperazine-1-carboxylate (350 mg, 0.880 mmol, 1.00 equiv) and dichloromethane (5 mL). Trifluoroacetic acid (0.5 mL) was added dropwise at 0° C. The resulting solution was stirred for 5 h at room temperature. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of water (10 mL). The resulting solution was extracted with dichloromethane (3×10 mL) and the organic layers were combined, washed with brine (2×10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 270 mg (crude) of 1-[[4-(2,6-dimethylpyridin-4-yl)-2-methylphenyl]methyl]piperazine as yellow oil. LCMS (ESI, m/z): 296 [M+H]+.

Workup

  1. temperatureA 50 mL round-bottom flask maintained with an inert atmosphere of nitrogen
  2. customThe reaction was then quenched by the addition of water (10 mL)
  3. extractionThe resulting solution was extracted with dichloromethane (3×10 mL)
  4. washwashed with brine (2×10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-706b08212e6d4d04ba741378008a7792
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

Loading…