Methylamine → 5-[5-(4-Aminobutyl)pyridin-2-YL]-N-methylpentanamide

HRID 860068Notes

Reaction equation

HRID 860068 reaction equation
C(O[C:4](=[O:30])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:11][N:10]=1)C.[CH3:31][NH2:32]>CO>[CH3:31][NH:32][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 235812725-{5-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-pyridin-2-yl}-pentanoic acid ethyl ester

Product 1

HCID 220826725-[5-(4-Aminobutyl)pyridin-2-YL]-N-methylpentanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 8-6 (45 g, 110 mmol) and a saturated solution of methylamine in methanol (300 mL) in a sealed tube was heated at 70° C. for 12 hours. The mixture was cooled and concentrated to an oil. The residue was chromatographed on silica gel (10:10:1:1 EtOAc/EtOH/NH4OH/H2O) to give 8-7 as a yellow oil.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated to an oil
  3. customThe residue was chromatographed on silica gel (10:10:1:1 EtOAc/EtOH/NH4OH/H2O)

Sources & evidence

ORD record
ord-bab5696bd30641b6939529f38daef037
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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