Hydrochloric Acid → (S)-(4-benzylmorpholin-2-yl)methanol

HRID 1478553Notes

Reaction equation

HRID 1478553 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC[C@H]1[CH2:16][O:15]1.Cl.O.[CH3:19][CH:20](O)C>O>[CH2:1]([N:8]1[CH2:20][CH2:19][O:11][C@H:10]([CH2:16][OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4348BenzylethanolamineHCID 2734062(-)-EpichlorohydrinHCID 21889133Propan-2-ol--water (1/1)

Product 1

HCID 736507(S)-(4-benzylmorpholin-2-yl)methanolYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(benzylamino)ethanol 38.3 ml (270.22 mmnol) and (R)-2-(chloromethyl)oxirane 25 g (270.22 mmnol) were dissolved in H2O/IPA (26 ml+26 ml), and stirred at room temperature overnight. After that, 130 ml of Et3NOH (35%) dissolved in water was slowly dropped over 1 hour, and stirred at room temperature for 3 hours. After the completion of the reaction, the reaction mixture was adjusted to pH 9 with 1 N HCl, followed by extraction using H2O and EA, drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:1), to give (S)-(4-benzylmorpholin-2-yl)methanol as a colorless oil (50%).

Workup

  1. additionwas slowly dropped over 1 hour
  2. stirringstirred at room temperature for 3 hours
  3. customAfter the completion of the reaction
  4. extractionfollowed by extraction
  5. customdrying
  6. filtration(Na2SO4), filtration, and concentration under reduced pressure
  7. customthe residue was purified by column chromatography (EA:Hex=1:1)

Sources & evidence

ORD record
ord-dfc3c372fb814794921a5873b0c80278
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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