Morpholine → HCID 68996601, compound

HRID 1987997Notes

Reaction equation

HRID 1987997 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]2[C:6](=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:10][CH:11]=2)[N:7]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>CN(C=O)C>[O:19]1[CH2:20][CH2:21][N:16]([CH2:2][C:3]2[O:4][C:5]3[C:6](=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:10][CH:11]=3)[N:7]=2)[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 689963151006601-77-9

Product 1

HCID 68996601HCID 68996601, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from Step B (281 mg, 1.24 mmol) and morpholine (2.0 mL, 23 mmol) in DMF (10 mL) was stirred at ambient temperature for 16 h. The solvent was removed under reduced pressure and the residue was treated with ethyl acetate (10 mL). The formed precipitate was filtered off and mother liquor was concentrated under reduced pressure to afford methyl 2-(morpholinomethyl)benzoxazole-4-carboxylate (333 mg, 97%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.01 (dd, J=9.0, 1.0 Hz, 1H), 7.74 (dd, J=9.0, 1.0 Hz, 1H), 6.40 (t, J=7.8 Hz, 1H), 4.02 (s, 2H), 3.97 (s, 3H), 3.78-3.74 (m, 4H), 2.69-2.65 (m, 4H); MS (ESI+) m/z 277 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was treated with ethyl acetate (10 mL)
  3. filtrationThe formed precipitate was filtered off
  4. concentrationmother liquor was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e0da59c294e4480e97d5f73c28b0fdb9
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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