Morpholine → (4-Ethynylphenyl)(morpholino)methanone

HRID 76182Notes

Reaction equation

HRID 76182 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=CC=CC=2C(O)=O)=[CH:5][CH:4]=1)#C.C1N=CN(C(N2C=NC=C2)=[O:24])C=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C1COCC1>[C:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[O:24])=[CH:8][CH:7]=1)#[CH:17]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 866696224-Ethynylphenyl benzoic acid

Product 1

HCID 57764578(4-Ethynylphenyl)(morpholino)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 3.50 g (23.9 mmol) 4-ethynylphenyl benzoic acid in 20 mL THF are added 3.88 g (23.9 mmol) CDI. The mixture is stirred at 60° C. for 30 min and then charged with 2.11 mL (23.9 mmol) morpholine. The complete mixture is stirred under reflux for 5 h and at r.t. for 24 h. The solvent is removed in vacuo and the residue is purified by column chromatography (silica gel, EtOAc 100%).

Workup

  1. stirringThe complete mixture is stirred
  2. temperatureunder reflux for 5 h and at r.t. for 24 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by column chromatography (silica gel, EtOAc 100%)

Sources & evidence

ORD record
ord-35823a5ab5454fde9adccc40d3707835
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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