2-chloro-N-(3-(dibenzylamino)-2-hydroxypropyl)acetamide → 6-((Dibenzylamino)methyl)morpholin-3-one

HRID 57598Notes

Reaction equation

HRID 57598 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH:7]([OH:24])[CH2:8][N:9]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:4].CC([O-])(C)C.[K+]>CC(O)(C)C>[CH2:10]([N:9]([CH2:8][CH:7]1[CH2:6][NH:5][C:3](=[O:4])[CH2:2][O:24]1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 117252152-chloro-N-(3-(dibenzylamino)-2-hydroxypropyl)acetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 99955506-((Dibenzylamino)methyl)morpholin-3-one

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 2-chloro-N-(3-(dibenzylamino)-2-hydroxypropyl)acetamide (1.0 g, 2.49 mmol), t-BuOK (0.39 g, 3.57 mmol) in t-BuOH (30 mL) was stirred at reflux overnight. After concentration, the residue was purified by column chromatography to give product as white solid.

Workup

  1. temperatureat reflux overnight
  2. concentrationAfter concentration
  3. customthe residue was purified by column chromatography
  4. customto give product as white solid

Sources & evidence

ORD record
ord-3554ed25db0f4d5a8f454c2d718e4f90
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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