Dimethylformamide → Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(dimethylamino)benzoate

HRID 1787914Notes

Reaction equation

[CH3:1][N:2](C=O)[CH3:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([O:19][C:20]2[CH:29]=[C:28](F)[CH:27]=[CH:26][C:21]=2[C:22]([O:24][CH3:25])=[O:23])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].N1CCOCC1.C([O-])([O-])=O.[Cs+].[Cs+]>[Cl-].[Na+].O>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([O:19][C:20]2[CH:29]=[C:28]([N:2]([CH3:3])[CH3:1])[CH:27]=[CH:26][C:21]=2[C:22]([O:24][CH3:25])=[O:23])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 110 °C

Procedure

The 4-dimethylamino compound was obtained in the following preparation in which the dimethylamino group was derived from in situ decomposition of the solvent DMF: A mixture of methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoate (6.45 g, 18.25 mmol), morpholine (8 g, 91.26 mmol), Cs2CO3 (11.8 g, 36.5 mmol), and DMF (10 mL) was heated 3 days at 110° C. The reaction mixture was poured into brine (100 mL) and extracted with EtOAc (3×100 mL). The combined extracts were washed with brine (3×200 mL), dried over MgSO4, and concentrated to an oil which was purified by chromatography on silica using 25% EtOAc in hexanes to give 4.1 g (59%) of product as a white solid.

Workup

extractionextracted with EtOAc (3×100 mL)
washThe combined extracts were washed with brine (3×200 mL)
dry with materialdried over MgSO4
concentrationconcentrated to an oil which
customwas purified by chromatography on silica using 25% EtOAc in hexanes

Sources & evidence

ORD record: ord-d3a29ac2466649be9f7409d0a2015af4
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511066B2

Reaction notes

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