2-Pyridinemethanamine → Methyl 4-(2-(2-picolylamino)ethyl)benzoate

HRID 11841

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH2:8].C(N(C(C)C)CC)(C)C.Br[CH2:19][CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][CH2:19][CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Commercially available 2-picolylamine (0.625 ml) was dissolved in toluene (15 ml) and diisopropylethylamine (0.715 ml) was added. After the addition of the compound obtained in Example 9-1 (499.7 mg), the mixture was stirred for two days at 80° C. After the reaction, toluene was added. The solution was washed with distilled water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by istillation under reduced pressure, and the residue was purified by silica gel column chromatography (25 g, chloroform/methanol=25/1) to obtain the title compound (400.1 mg) as light brown oil.

Workup

additionwas added
washThe solution was washed with distilled water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed by istillation under reduced pressure
customthe residue was purified by silica gel column chromatography (25 g, chloroform/methanol=25/1)

Sources & evidence

ORD record: ord-a78758e5b0fc4b538301b9f611812224
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098215B2

Linked notes

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