Water → Phenylmethyl 2-acetyl-4-morpholinecarboxylate

HRID 1527134Notes

Reaction equation

HRID 1527134 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([C:7](=[O:9])[CH3:8])[CH2:2]1.C(N(CC)CC)C.[C:17](Cl)(=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C(Cl)Cl>[C:7]([CH:3]1[O:4][CH2:5][CH2:6][N:1]([C:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:26])[CH2:2]1)(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 10387Benzyl chloroformateHCID 222635521-Morpholin-2-YL-ethanone

Product 1

HCID 18354411Phenylmethyl 2-acetyl-4-morpholinecarboxylateYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(morpholin-2-yl)ethanone (3.9 g, 30.0 mmol) in DCM (60 mL) was added triethylamine (1.0 g, 10 mmol) to adjust pH 9. Then benzyl carbonochloridate (5.6 g, 33.0 mmol) and triethylamine (3.0 g, 30.0 mmol) were added and the mixture was stirred at room temperature for 16 hr. The reaction solution was added H2O (20 mL) and extracted by DCM (100 mL*3). The organic layer was concentrated and purified by column chromatography on silica gel (eluted: petroleum ether/ethyl acetate=20/1-15/1-10/1) to give benzyl 2-acetylmorpholine-4-carboxylate (5.0 g, 63%).

Workup

  1. extractionextracted by DCM (100 mL*3)
  2. concentrationThe organic layer was concentrated
  3. custompurified by column chromatography on silica gel (eluted: petroleum ether/ethyl acetate=20/1-15/1-10/1)

Sources & evidence

ORD record
ord-25736160993c46c7b16a3fd82de7aa72
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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