Dimethylformamide → Methyl 2-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)acetate

HRID 253602Notes

Reaction equation

HRID 253602 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1.Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CCOC(C)=O>[CH3:2][O:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:10]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 668619713-((3-Methoxypropoxy)(phenyl)methyl)piperidine hydrochloride

Product 1

HCID 57786482Methyl 2-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)acetateYield 27%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-((3-Methoxypropoxy)(phenyl)methyl)piperidine HCl salt (63 mg, 0.212 mmol) was mixed with methyl bromoacetate (20 μL), K2CO3 (75 mg, 2.5 equiv.), and anhydrous DMF (3 mL). The mixture was stirred overnight at rt. LC-MS indicated the reaction was complete. The mixture was diluted with EtOAc and washed with water. The water layer was extracted with EtOAc. The combined organic layers were washed with water and brine, and dried over Na2SO4. After concentration, the residue was purified by flash chromatography on a 4-g silica gel cartridge eluted with a 0-10% methanol in dichloromethane gradient to afford methyl 2-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)acetate (19 mg, 27% yield). LC-MS (3 min) tR=1.07 min, m/z 336 (M+1).

Workup

  1. washwashed with water
  2. extractionThe water layer was extracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe residue was purified by flash chromatography on a 4-g silica gel cartridge
  7. washeluted with a 0-10% methanol in dichloromethane gradient

Sources & evidence

ORD record
ord-fb7e025a645648d28fba30e78bd34132
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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