Trifluoroacetic acid → 6-[(4-Methylpiperazin-1-yl)methyl]pyridin-2-amine

HRID 1504769Notes

Reaction equation

HRID 1504769 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[N:14]=[C:13]([NH:15]C(=O)OC(C)(C)C)[CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[N:14]=[C:13]([NH2:15])[CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86731662Tert-butyl {6-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl}carbamate

Product 1

HCID 120778076-[(4-Methylpiperazin-1-yl)methyl]pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {6-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl}carbamate (103 mg, 0.337 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (1.2 mL, 16 mmol) at room temperature. After 3 hours, the reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium carbonate was added to adjust to pH˜9. The mixture was then extracted with ethyl acetate (3×) and the combined organics were dried over magnesium sulfate, filtered, and concentrated to afford 6-[(4-methylpiperazin-1-yl)methyl]pyridin-2-amine that was used without further purification. MS ESI calc'd for C11H19N4 [M+H]+ 207. found 207. 1H NMR (500 MHz, CD3OD) δ 7.46-7.40 (m, 1H), 6.66 (d, J=7.2 Hz, 1H), 6.47 (d, J=8.3 Hz, 1H), 3.47 (s, 2H), 2.85-2.46 (m, 8H), 2.39 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium carbonate
  2. additionwas added
  3. extractionThe mixture was then extracted with ethyl acetate (3×)
  4. dry with materialthe combined organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e6f478455261498c8e61948a43e9e958
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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