Diisopropylethylamine → HCID 66805330, compound

HRID 1193315Notes

Reaction equation

HRID 1193315 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:10]1[CH2:14][CH2:13][NH:12][CH2:11]1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.CCN(C(C)C)C(C)C>CC(O)C.C([O-])(O)=O.[Na+]>[CH3:9][N:8]([CH:10]1[CH2:14][CH2:13][N:12]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH2:11]1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 818524-Chloropyridine hydrochlorideHCID 27614043-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidine

Product 1

HCID 66805330HCID 66805330, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-(N-Tert-butoxycarbonyl-N-methylamino)pyrrolidine (4.993 mmol, 1 eq) and 4-chloropyridine hydrochloride (14.979 mmol, 3 eq) were dissolved in 2-propanol (15 ml) and DIPEA (19.972 mmol, 4 eq) and refluxed for 16 h. After monitoring by thin-layer chromatography, the reaction solution was diluted with sat. NaHCO3 solution and extracted with ethyl acetate (3×20 ml). The combined org. phases were washed with sat. NaCl solution, dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography (silica gel, ethyl acetate:ethanol 10:1+ammonia (25% aq)). Yield: 61%.

Workup

  1. extractionextracted with ethyl acetate (3×20 ml)
  2. washphases were washed with sat. NaCl solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (silica gel, ethyl acetate:ethanol 10:1+ammonia (25% aq))

Sources & evidence

ORD record
ord-2f23b07705804ff0a657fce41c1ae33a
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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