Trifluoroacetic acid → 6-(Morpholin-4-ylmethyl)pyridin-2-amine

HRID 1504767Notes

Reaction equation

HRID 1504767 reaction equation
[N:1]1([CH2:7][C:8]2[N:13]=[C:12]([NH:14]C(=O)OC(C)(C)C)[CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[N:1]1([CH2:7][C:8]2[N:13]=[C:12]([NH2:14])[CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67025080HCID 67025080, compound

Product 1

HCID 120778096-(Morpholin-4-ylmethyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [6-(morpholin-4-ylmethyl)pyridin-2-yl]carbamate (114 mg, 0.39 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 extracted with ethyl acetate (3×), and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 6-(morpholin-4-ylmethyl)pyridin-2-amine that was used without further purification. MS ESI calc'd for C10H16N3O [M+H]+ 194. found 194. 1H NMR (500 MHz, DMSO-d6) δ 7.32 (t, J=7.7 Hz, 1H), 6.52 (d, J=7.2 Hz, 1H), 6.30 (d, J=8.2 Hz, 1H), 5.90 (s, 2H), 3.63-3.49 (m, 4H), 3.40-3.25 (m, 2H), 2.41 (s, 4H).

Workup

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

Sources & evidence

ORD record
ord-7c7ef1439fbe49a79fce36da6a0b4fe6
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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