Morpholine → 4-(morpholinomethyl)benzoic acid

HRID 252848Notes

Reaction equation

HRID 252848 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C1COCC1>[O:15]1[CH2:16][CH2:17][N:12]([CH2:2][C:3]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 225994-(Bromomethyl)benzoic acid

Product 1

HCID 7035074-(morpholinomethyl)benzoic acidYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-bromomethyl-benzoic acid (239, 1.5 g, 6.78 mmol) in THF (15 mL) was added morpholine (0.61 mL, 6.78 mmol). The reaction mixture was allowed to stir for 10 minutes before the resulting white precipitate was filtered off and discarded. The filtrate was evaporated under reduced pressure and the remaining solid was dried under vacuum to afford the title compound 240 as a white solid (1.15 g, 75% yield). 1H NMR: (DMSO) δ 7.89-7.86 (m, 2H), 7.52 (d. J=8.4 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 4.12 (s, 2H), 3.75-3.72 (m, 1H), 3.56-3.58 (m, 4H), 3.10-3.07 (m, 1H), 2.45-2.35 (m, 2H).

Workup

  1. filtrationwas filtered off
  2. customThe filtrate was evaporated under reduced pressure
  3. customthe remaining solid was dried under vacuum

Sources & evidence

ORD record
ord-5ab56e8b75974738a0d3c6df8995caf9
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

Loading…