Sodium Hydroxide → 2-(3,5-Dichlorophenyl)morpholine

HRID 530638Notes

Reaction equation

HRID 530638 reaction equation
C(O)(=O)C(O)=O.[Cl:7][C:8]1[CH:9]=[C:10]([CH:15]2[O:20][CH2:19][CH2:18][NH:17][CH2:16]2)[CH:11]=[C:12]([Cl:14])[CH:13]=1.[OH-].[Na+]>ClCCl>[Cl:14][C:12]1[CH:11]=[C:10]([CH:15]2[O:20][CH2:19][CH2:18][NH:17][CH2:16]2)[CH:9]=[C:8]([Cl:7])[CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 177498082-(3,5-Dichlorophenyl)morpholine oxalate

Product 1

HCID 50201412-(3,5-Dichlorophenyl)morpholineYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3,5-Dichlorophenyl)morpholine oxalate (1 g) from Chem-Impex was added to 5% aq NaOH and dichloromethane and extracted (3×100 mL dichloromethane). Combined extracts were dried over Na2SO4, filtered and concentrated to afford 728 mg of 2-(3,5-dichlorophenyl)morpholine as the free-base. In a 100 mL round-bottom flask, 2-(3,5-dichlorophenyl)morpholine (728 mg, 3.14 mmol) and (S)-2-(trifluoromethyl)oxirane (527 mg, 4.7 mmol) were combined with acetonitrile (10.0 ml) to give a yellow solution. Stirring was continued at room temperature for 3 days. Reaction mixture was concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 5% to 20% EtOAc in hexanes) to afford (2S)-3-(2-(3,5-dichlorophenyl)morpholino)-1,1,1-trifluoropropan-2-ol (1.06 g, 98%) as a colorless oil. (M+H)+=344, 346 m/e. Used as is.

Workup

  1. extractionextracted (3×100 mL dichloromethane)
  2. dry with materialCombined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5080f5c16a304e0a83d2fc2928bafc5a
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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