Dimethylformamide → Methyl 3-[4-({4-[(4-hydroxypiperidin-1-yl)methyl]benzyl}oxy)phenyl]propanoate

HRID 2110902Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[OH:23][CH:24]1[CH2:29][CH2:28][N:27]([CH2:2][C:3]2[CH:22]=[CH:21][C:6]([CH2:7][O:8][C:9]3[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=3)=[CH:5][CH:4]=2)[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 3-(4-{[4-(chloromethyl)benzyl]oxy}phenyl)propanoate (0.6 g, 1.88 mmol), 4-hydroxypiperidine (0.29 g, 2.82 mmol), potassium carbonate (0.39 g, 2.82 mmol) and N,N-dimethylformamide (12 mL) was stirred at 60° C. for 21 hr. The reaction mixture was diluted with ethyl acetate, and the mixture washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (0.72 g, yield 99%) as a beige powder. MS (ESI+): 384 (M+H).

Workup

washthe mixture washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-74d86cbe99464fb29f8c016a18749283
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517910B2

Reaction notes

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