Potassium Carbonate → tert-Butyl 4-(4-(pyridin-4-ylmethyl)piperazin-1-yl)benzoate

HRID 1907758Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:3][CH:2]=1.[C:14]([O:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CCOC(C)=O.O>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([O:18][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:27])=[CH:21][CH:22]=3)[CH2:10][CH2:9]2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 1-[(4-Pyridyl)methyl]piperazine (1.00 g, 5.6 mmol) in DMSO (4.5 mL) in a pressure vessel was added t-butyl-4-fluorobenzoate (1.05 g, 5.4 mmol) followed by potassium carbonate (0.74 g, 5.4 mmol). The pressure vessel was closed and the mixture was stirred at 130° C. for 21 h. The mixture was diluted with EtOAc (300 mL) and water (50 mL). The organic layer was separated, washed with a saturated NaHCO3 solution, brine, dried over MgSO4, and concentrated in vacuo. The residue obtained was purified by flash chromatography using 0-5% MeOH in DCM to afford the title compound 338 as a pink solid (1.34 g, 71% yield).

Workup

customThe pressure vessel was closed
customThe organic layer was separated
washwashed with a saturated NaHCO3 solution, brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue obtained
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-884ada67a00144809336a912fd64f7f5
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598168B2

Reaction notes

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