Trifluoroacetic acid → 6-((Morpholin-4-yl)methyl)pyridin-3-amine

HRID 85164Notes

Reaction equation

HRID 85164 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[N:13]=[CH:12][C:11]([NH:14]C(=O)OC(C)(C)C)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>ClCCl>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[N:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67170692(6-Morpholin-4-ylmethyl-pyridin-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 207248406-((Morpholin-4-yl)methyl)pyridin-3-amineYield 56.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-(morpholinomethyl)pyridin-3-ylcarbamate (115; 1.20 g, 4.1 mmol) in dichloromethane (20 mL) was added TFA (6.0 mL). The resulting reaction mixture was stirred at room temperature for 12 h and then concentrated under reduced pressure. Enough saturated aqueous Na2CO3 was added to the residue to adjust the pH=9. The mixture was extracted with ethyl acetate (3×25 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford 6-(morpholinomethyl)pyridin-3-amine 116 (450 mg, 56%).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. additionEnough saturated aqueous Na2CO3 was added to the residue
  4. extractionThe mixture was extracted with ethyl acetate (3×25 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c51fc45677b4a278e3ebf96bd6cb938
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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