Ethyl Acetate → 2-(1-Benzylpiperidin-4-ylamino)-5-methylpyridine

HRID 2223873Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6](C)[CH:5]=[CH:4][N:3]=1.[NH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.[C:23](OCC)(=O)C.C(=O)(O)[O-].[Na+]>O>[CH2:16]([N:13]1[CH2:14][CH2:15][CH:10]([NH:9][C:2]2[CH:7]=[CH:6][C:5]([CH3:23])=[CH:4][N:3]=2)[CH2:11][CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To 2-bromo-4-methylpyridine (15.5 g) was added 4-amino-1-benzylpiperidine (68.5 g). The resulting solution was stirred at 180° C. for 9 hours and then at 150° C. for 6 hours. Ethyl acetate and water were then added to the solution followed by addition of saturated aqueous sodium bicarbonate solution. After separating liquid layers, the organic layer was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, ethyl acetate-methanol-aqueous ammonia (90:10:0.1)] to give the title compound (11.5 g).

Workup

waitat 150° C. for 6 hours
customAfter separating liquid layers
washthe organic layer was washed with water and saturated aqueous sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by chromatography [silica gel, ethyl acetate-methanol-aqueous ammonia (90:10:0.1)]

Sources & evidence

ORD record: ord-d660c6c007a742718f1d7d9b80c272a8
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375115B2

Reaction notes

Loading…