Triethylamine → HCID 57743093, compound

HRID 1924349Notes

Reaction equation

HRID 1924349 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:11][CH2:12][CH:13]([CH2:20][CH2:21][CH3:22])[CH2:14][C:15](OCC)=[O:16].C(N(CC)CC)C.[BH4-].[Na+]>CCO>[NH2:1][C:2]1[C:3]([CH2:4][N:11]2[CH2:12][CH:13]([CH2:20][CH2:21][CH3:22])[CH2:14][C:15]2=[O:16])=[CH:6][CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 4311764Sodium borohydrideHCID 53629151HCID 53629151, compound

Product 1

HCID 57743093HCID 57743093, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-aminonicotinaldehyde x282 (8.19 mmol, 1 eq, 1 g) in 10 ml of EtOH, is added ethyl 3-(aminomethyl)hexanoate hydrochloride x31 (9.83 mmol, 1.2 eq, 2.06 g) and the resulting solution is stirred at room temperature for 1 h30. Then, triethylamine (9.0 mmol, 1.1 eq, 909 mg) is added and the mixture is stirred during 0.5 hour. Sodium borohydride is then added (9.83 mmol, 1.2 eq, 372 mg). The resulting mixture is stirred at room temperature for 20 hours, heated at 55° C. for 21 hours and then overnight at room temperature. Volatiles are removed under vacuum and CH2Cl2 (50 ml) and water (25 ml) are added. The organic layer is washed with water (25 ml) and dried over MgSO4. After filtration, volatiles are removed under reduced pressure. The crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH 98/2/0.2 (v/v/v)) and recrystallized in AcOEt to afford 1-[(2-aminopyridin-3-yl)methyl]-4-propylpyrrolidin-2-one 230 as a white solid (152 mg).

Workup

  1. stirringthe mixture is stirred during 0.5 hour
  2. stirringThe resulting mixture is stirred at room temperature for 20 hours
  3. temperatureheated at 55° C. for 21 hours
  4. customovernight
  5. customat room temperature
  6. customVolatiles are removed under vacuum and CH2Cl2 (50 ml) and water (25 ml)
  7. additionare added
  8. washThe organic layer is washed with water (25 ml)
  9. dry with materialdried over MgSO4
  10. filtrationAfter filtration, volatiles
  11. customare removed under reduced pressure
  12. customThe crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH 98/2/0.2 (v/v/v))
  13. customrecrystallized in AcOEt

Sources & evidence

ORD record
ord-31fbbd494a83492bbaf889b1f5ba7402
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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