Morpholine → Ethyl 3-{[2-(4-morpholinyl)ethyl]oxy}benzoate

HRID 2168220Notes

Reaction equation

HRID 2168220 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[N:16]1([CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 54408639Ethyl 3-(2-bromoethoxy)benzoate

Product 1

HCID 58089039Ethyl 3-{[2-(4-morpholinyl)ethyl]oxy}benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 3-[(2-bromoethyl)oxy]benzoate D46 (100 mg), morpholine (44.7 mg, 0.513 mmol) in Acetonitrile (2 mL) stirred under nitrogen at 25° C. was added K2CO3 (106 mg, 0.769 mmol). The reaction mixture was stirred at 60° overnight. The mixture was filtered and the filtrate was concentrated in vacuo to give 98 mg of the crude product D47 without more purification. LCMS Retention time=1.57 mins, [M+H]+280 (5 min run)

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-52824f249af94e7f847ae62d7ad12bb8
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

Loading…