Dimethylamine → 2-(4-Benzoylphenoxymethyl)-2-[(dimethylamino)methyl]propane-1,3-diol

HRID 531397Notes

Reaction equation

HRID 531397 reaction equation
Br[CH2:2][C:3]([CH2:22][OH:23])([CH2:20][OH:21])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[CH:8][CH:7]=1.[CH3:24][NH:25][CH3:26]>C(O)C>[C:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([CH2:2][N:25]([CH3:26])[CH3:24])([CH2:22][OH:23])[CH2:20][OH:21])=[CH:7][CH:8]=1)(=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 89907389{4-[3-Bromo-2,2-bis(hydroxymethyl)propoxy]phenyl}(phenyl)methanone

Product 1

HCID 899083732-(4-Benzoylphenoxymethyl)-2-[(dimethylamino)methyl]propane-1,3-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve the {4-[3-bromo-2,2-bis(hydroxymethyl)propoxy]phenyl}(phenyl)methanone obtained in the previous stage in ethanol and treat it with excess of 40% aq. dimethylamine at reflux for 8 h. Remove the solvent in vacuo and purify the residue by column chromatography to provide the desired 2-(4-benzoylphenoxymethyl)-2-[(dimethylamino)methyl]propane-1,3-diol.

Workup

  1. temperatureat reflux for 8 h
  2. customRemove the solvent in vacuo
  3. custompurify the residue by column chromatography

Sources & evidence

ORD record
ord-40e4cc2a140846ec80f53c973e568b26
Source dataset
uspto-grants-2016_05
Patent number
US09353211B2

Reaction notes

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