Diethyl Ether → HCID 53927178, compound

HRID 1458532Notes

Reaction equation

HRID 1458532 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH:9]([NH:16][CH2:17][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[OH:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.C[CH2:27][O:28]CC.[OH-].[Na+].ClC(OC(Cl)(Cl)Cl)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][CH:9]([N:16]2[CH2:17][CH:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:19][C:27]2=[O:28])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10426DiphosgeneHCID 14798Sodium HydroxideHCID 54140316HCID 54140316, compound2×

Product 1

HCID 53927178HCID 53927178, compoundYield 16.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3-Morpholino-1-phenylpropyl)amino-1-phenylethanol (2.2 g, 6.46 mmol) prepared in the above (1), ether (100 ml) and 10% NaOH (50 ml) were mixed and stirred. To the obtained mixture, 20% toluene solution of trichloromethyl chloroformate [14 ml (14 mmol)] was dropwise added slowly for a period of 1 hour. After stirring at room temperature for 1 hour, ethyl acetate (200 ml) was added to the resulting solution, and then the ethyl acetate portion was collected. The obtained portion was washed with saturated aqueous sodium chloride (100 ml) and then dried over anhydrous sodium sulfate. After the solvent was removed by distillation under reduced pressure, the residue was purified by medium pressure silica gel column chromatography (chloroform/methanol=50/1) to obtain 510 mg of diastereomer A (yield: 21.5%) and 390 mg of diastereomer B (yield: 16.5%) of the titled compound as oily products, provided that the diastereoisomers showing the Rf values of about 0.6 and 0.5 in TLC (chloroform/methanol=10/1) were referred to as diastereoisomers A and B, respectively.

Workup

  1. additionwere mixed
  2. stirringAfter stirring at room temperature for 1 hour
  3. customthe ethyl acetate portion was collected
  4. washThe obtained portion was washed with saturated aqueous sodium chloride (100 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter the solvent was removed by distillation under reduced pressure
  7. customthe residue was purified by medium pressure silica gel column chromatography (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-00a1ec7502a643acb14c4f2f4fcb5ea1
Source dataset
uspto-grants-1998_12
Patent number
US05852006

Reaction notes

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