4-(Pyrrolidin-1-yl)butan-1-amine → 4-Chloro-N-[4-(1-pyrrolidinyl)butyl]-2-pyridinecarboxamide

HRID 491678

Reaction equation

HRID 491678 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[N:11]1([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH2:15][CH2:14][CH2:13][CH2:12]1>C1COCC1.CCOC(C)=O>[N:11]1([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:8]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=2)=[O:9])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 27627624-(Pyrrolidin-1-yl)butan-1-amineHCID 110951464-chloropyridine-2-carbonyl Chloride

Product 1

HCID 859719314-Chloro-N-[4-(1-pyrrolidinyl)butyl]-2-pyridinecarboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-chloro-pyridine-2-carbonyl chloride (8.88 g, 49 mmol) in THF (100 mL) was added at 0° C. 4-pyrrolidin-1-yl-butylamine (7.0 g, 49 mmol). The reaction was stirred for 18 h at RT. The mixture was diluted with EtOAc, washed several time with aqueous 6 N NaOH and then brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography using a gradient CH2Cl2/MeOH/NH4OH (100%, 0%, 0% to 90%, 10%, 1%). The pure fractions were combined and the solvents removed under vacuum. The title compound was obtained.

Workup

  1. additionwas added at 0° C
  2. washwashed several time with aqueous 6 N NaOH
  3. dry with materialbrine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography
  7. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-62815154662f40f2b6291db7c0c97d64
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Linked notes

Loading…