Morpholine → 2-[2-(Morpholinomethyl)phenyl]acetic acid

HRID 2357331Notes

Reaction equation

HRID 2357331 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C1COCC1.C(OCC)(=O)C>[O:16]1[CH2:17][CH2:18][N:13]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[CH2:9][C:10]([OH:12])=[O:11])[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 98154412-(CHLOROMETHYL)PHENYLACETIC ACID

Product 1

HCID 138848022-[2-(Morpholinomethyl)phenyl]acetic acidYield 87.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-(2-(chloromethyl)phenyl)acetic acid (2.00 g, 10.8 mmol) in THF (20 mL) was added morpholine (1.89 g, 21.7 mmol) and the solution was stirred at room temperature for 3 hours. The reaction mixture was then diluted with ethyl acetate and extracted with H2O (2×). The aqueous phase was lyophilized and the residue was purified by silica gel chromatography (Biotage/0-10% methanol-CH2Cl2) to give the title compound 2-(2-(Morpholinomethyl)phenyl)acetic acid as a colorless solid (2.22 g, 87%). 1HNMR (400 MHz, CD3OD) δ 7.37-7.44 (m, 3H), 7.29-7.33 (m, 1H), 4.24 (s, 2H), 3.83 (br s, 4H), 3.68 (s, 2H), 3.14 (br s, 4H). LCMS: Anal. Calcd. for C13H17NO3: 235; found: 236 (M+H)+.

Workup

  1. extractionextracted with H2O (2×)
  2. customthe residue was purified by silica gel chromatography (Biotage/0-10% methanol-CH2Cl2)

Sources & evidence

ORD record
ord-68361a61dee34b7fb600c907acf94a82
Source dataset
uspto-grants-2010_07
Patent number
US07759495B2

Reaction notes

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