Morpholine → HCID 21069934, compound

HRID 1726560Notes

Reaction equation

HRID 1726560 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:24])=[C:19]([CH:23]=1)[C:20](Cl)=[O:21]>C(Cl)Cl>[F:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:24])=[C:19]([C:20]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:21])[CH:23]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 27373835-Fluoro-2-methylbenzoyl chloride

Product 1

HCID 21069934HCID 21069934, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of morpholine (870 mg, 10 mmol) and triethylamine (1.1 g, 10.8 mmol) in CH2Cl2 (15 mL) was added a solution of 5-fluoro-2-methylbenzoyl chloride (1.72 g, 10 mmol) in CH2Cl2 (5 mL), dropwise, and the mixture stirred for 15 min. The mixture was then washed with water, and the organic phase dried (MgSO4), filtered, and concentrated to obtain 2.19 g (Yield 98%) of the title compound as a solid: 1H NMR (500 MHz, CDCl3) δ ppm: 2.27 (3H, s) 3.24 (2H, d, J=4 Hz) 3.58 (2H, s) 3.79 (4H, dd, J=18, 3.8 Hz) 6.88 (1H, dd, J=8.2, 2.8 Hz) 6.92-7.05 (1H, m) 7.18 (1H, dd, J=8.4, 5.3 Hz).

Workup

  1. washThe mixture was then washed with water
  2. dry with materialthe organic phase dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ddc195f194f44755a8daed0188c81111
Source dataset
uspto-grants-2009_02
Patent number
US07491819B1

Reaction notes

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