Ammonia → HCID 13048847, compound

HRID 1076645Notes

Reaction equation

HRID 1076645 reaction equation
[Mg].[CH3:2][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1.[OH:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][O:17][CH:16]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+].N>CCOCC>[OH:12][CH2:13][CH2:14][N:15]([CH:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:8][C:7]1[CH:10]=[CH:11][C:4]([O:3][CH3:2])=[CH:5][CH:6]=1)[CH2:19][CH2:18][OH:17]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 699934-Methyloxybenzyl chlorideHCID 5462224Magnesium2×HCID 126486632-(2-Phenyl-1,3-oxazolidin-3-yl)ethan-1-ol

Product 1

HCID 13048847HCID 13048847, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a Grignard reagent prepared from magnesium turnings (6.7 g), magnesium powder (6.7 g) and p-methoxybenzyl chloride (18.1 g) in absolute ether (240 ml) is added dropwise a solution of 3-(2-hydroxyethyl)-2-phenyloxazolidine (9.6 g) in absolute ether (24 ml) under stirring, and the mixture is heated under reflux for 3 hours. The reaction mixture is poured onto ice water (100 ml) containing ammonium chloride under vigorously stirring by decantation, and the mixture is made alkaline with ammonia. The ether layer is separated and extracted with an excess amount of 10 % hydrochloric acid. The hydrochloric acid layer is made alkaline with sodium hydroxide and extracted with chloroform. The chloroform layer is dried over anhydrous sodium sulfate and then the solvent is distilled off to give an oily substance of crude N,N-bis(2-hydroxyethyl)-2-(4-methoxyphenyl)-1-phenylethylamine (10.2 g).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. additionThe reaction mixture is poured onto ice water (100 ml)
  4. stirringunder vigorously stirring by decantation
  5. customThe ether layer is separated
  6. extractionextracted with an excess amount of 10 % hydrochloric acid
  7. extractionextracted with chloroform
  8. dry with materialThe chloroform layer is dried over anhydrous sodium sulfate
  9. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-54aa85748a654efba4706072df3b578a
Source dataset
uspto-grants-1976_05
Patent number
US03957788

Reaction notes

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