Trifluoroacetic acid → 5-(morpholinomethyl)pyridin-2-amine

HRID 85160Notes

Reaction equation

HRID 85160 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([NH:14]C(=O)OC(C)(C)C)=[N:12][CH:13]=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[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67203903Tert-butyl 5-(morpholinomethyl)pyridin-2-ylcarbamate

Product 1

HCID 578675155-(morpholinomethyl)pyridin-2-amineYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-(morpholinomethyl)pyridin-2-ylcarbamate (107; 1.40 g, 4.77 mmol) in dichloromethane (10 mL) was added TFA (10.0 mL). The mixture was stirred at room temperature for 12 h. The reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 was added to the resulting residue to adjust the pH=9. The mixture was extracted with dichloromethane (3×25 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to afford 5-(morpholinomethyl)pyridin-2-amine 108 (0.85 g, 92%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionEnough saturated aqueous Na2CO3 was added to the resulting residue
  3. extractionThe mixture was extracted with dichloromethane (3×25 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f93a6da1ff1147729493f40161af7f69
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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