Trifluoroacetic acid → N-(4-aminobutyl)pyridin-2-amine

HRID 989892Notes

Reaction equation

HRID 989892 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 184195382-[[4-(Tert-butoxycarbonyl)amino-1-butyl]amino]pyridine

Product 1

HCID 14397369N-(4-aminobutyl)pyridin-2-amineYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude 2-[[4-(tert-butoxycarbonyl)amino-1-butyl]amino]pyridine (3.13 mmole) was treated with TFA (10 mL) in CH2Cl2 (10 mL). After 2 hr the mixture was concentrated under reduced pressure. The residue was taken up in 1.0 N NaOH (20 mL) and extracted with CHCl3 (4×50 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound (122 mg, 24%) as a yellow oil: MS (ES) m/e 166 (M+H)+.

Workup

  1. concentrationAfter 2 hr the mixture was concentrated under reduced pressure
  2. extractionextracted with CHCl3 (4×50 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7c1252197474e9eaa293e2b44bb7c5d
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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