Ammonia → HCID 20396937, compound

HRID 1679432Notes

Reaction equation

HRID 1679432 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][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br.[Cl-].[NH4+].N>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)[CH2:16][C:17]1[CH:18]=[C:19]([CH3:20])[CH:22]=[CH:23][CH:24]=1)[CH2:8][CH2:7][OH:6]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 12099m-Xylyl bromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 126486632-(2-Phenyl-1,3-oxazolidin-3-yl)ethan-1-ol

Product 1

HCID 20396937HCID 20396937, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3-(2-hydroxyethyl)-2-phenyloxazolidine (78 g) in anhydrous ether (300 ml) is added dropwise with stirring to Grignard reagent which is prepared from magnesium turnings (22 g) and m-methylbenzylbromide (150 g) in anhydrous ether (1200 ml), and the mixture is refluxed for 3 hours. After the reaction, the reaction mixture is decomposed with an ammonium chloride aqueous solution, and made alkaline with ammonia. The ether layer is separated and extracted with an excess amount of 10% hydrochloric acid. The aqueous layer is separated and made alkaline with sodium hydroxide and extracted with chloroform. The chloroform layer is dried over anhydrous sodium sulfate, and the solvent is distilled off to give crude dl-N,N-bis(2-hydroxyethyl)-1-phenyl-2-(3-tolyl)ethylamine (100 g) as an oily substance.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. customAfter the reaction
  3. customThe ether layer is separated
  4. extractionextracted with an excess amount of 10% hydrochloric acid
  5. customThe aqueous layer is separated
  6. extractionextracted with chloroform
  7. dry with materialThe chloroform layer is dried over anhydrous sodium sulfate
  8. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-2337377ce47a4b1eac5ab2f7e36064ea
Source dataset
uspto-grants-1978_03
Patent number
US04080453

Reaction notes

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