Triethylamine → Phenylmethyl 2-acetyl-4-morpholinecarboxylate

HRID 2206653Notes

Reaction equation

HRID 2206653 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>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

5

Reactant 3

HCID 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 1120 (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-a9e9f8e6eb8348049e46f5c4735674c1
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

Loading…