Potassium Carbonate → HCID 131730589, compound

HRID 2093587Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12](=[O:21])[NH:13][CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([CH3:10])([CH3:9])[CH3:8].Br[C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=1>CO>[C:7]([O:11][C:12](=[O:21])[NH:13][CH2:14][CH:15]1[CH2:16][CH2:17][N:18]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][N:24]=2)[CH2:19][CH2:20]1)([CH3:10])([CH3:8])[CH3:9]

Participants

Conditions

Temperature: 120 °C

Procedure

In a 5-ml microwave vial equipped was placed potassium carbonate (1.38 g), tert-butyl(piperidin-4-ylmethyl)carbamate (1.07 g), and 2-bromo-5-trifluoromethylpyridine (1.13 g) in methanol. This was heated to 120° C. for 30 min in a microwave reactor. The mixture was cooled and concentrated in vacuo, and the residue was taken up in ethyl acetate. This was filtered through a plug of silica gel, and the eluent was concentrated in vacuo to provide tert-butyl({1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}methyl)carbamate (1.45 g, 81%). This compound was taken up in 15 ml of dichloromethane and 15 ml of trifluoroacetic acid. The resultant mixture was stirred at room temperature for 2 h, and then concentrated and taken up in dichloromethane (20 ml) and saturated aqueous sodium bicarbonate. The mixture was extracted and the organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to provide 1.31 g (87%) of the title compound. Mass spectrum (ESI) 260.1 (M+1).

Workup

customIn a 5-ml microwave vial equipped
temperatureThe mixture was cooled
concentrationconcentrated in vacuo
filtrationThis was filtered through a plug of silica gel
concentrationthe eluent was concentrated in vacuo

Sources & evidence

ORD record: ord-442c14bc918343bf9334b186870f21db
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445480B2

Reaction notes

Loading…