Water → HCID 12466834, compound

HRID 972002Notes

Reaction equation

HRID 972002 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][O:6][CH:5]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Mg].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Cl.O>CCOCC>[OH:1][CH2:2][CH2:3][N:4]([CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[C:18]([O:17][CH3:16])[CH:19]=1)[CH2:8][CH2:7][OH:6]

Participants

6

Reactant 4

HCID 962WaterHCID 699943-Methoxybenzyl chlorideHCID 5462224MagnesiumHCID 126486632-(2-Phenyl-1,3-oxazolidin-3-yl)ethan-1-ol

Product 1

HCID 12466834HCID 12466834, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3-(2-hydroxyethyl)-2-phenyloxazolidine (11.0 g) in anhydrous ether (30 ml) is added dropwise with stirring to Grignard reagent which is prepared from magnesium turnings (3.3 g) and m-methoxybenzyl chloride (20.7 g) in anhydrous ether (150 ml), and the mixture is refluxed for 3 hours. After the reaction, the reaction mixture is decomposed by adding water thereto. The ether layer is separated and extracted with 10% hydrochloric acid (100 ml). The hydrochloric acid layer is made alkaline with ammonia and extracted with ether. The ether layer is dried over anhydrous sodium sulfate, and the solvent is distilled off to give crude dl-N,N-bis(2-hydroxyethyl)-2-(3-methoxyphenyl)-1-phenylethylamine (12.7 g) as an oily substance. When this substance is recrystallized from ethanol, it shows a melting point of 67°-69° C.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. customAfter the reaction
  3. customThe ether layer is separated
  4. extractionextracted with 10% hydrochloric acid (100 ml)
  5. extractionextracted with ether
  6. dry with materialThe ether layer is dried over anhydrous sodium sulfate
  7. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-773c1a4fdcdf4cc186578ec8aed55f66
Source dataset
uspto-grants-1979_07
Patent number
US04162316

Reaction notes

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