2-(3,5-Dichlorophenyl)morpholine → HCID 118276748, compound

HRID 530639Notes

Reaction equation

HRID 530639 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[O:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[F:15][C:16]([F:21])([F:20])[C@@H:17]1[CH2:19][O:18]1>C(#N)C>[Cl:8][C:6]1[CH:5]=[C:4]([CH:9]2[CH2:10][N:11]([CH2:19][C@H:17]([OH:18])[C:16]([F:21])([F:20])[F:15])[CH2:12][CH2:13][O:14]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 50201412-(3,5-Dichlorophenyl)morpholineHCID 7171781(2S)-2-(Trifluoromethyl)oxirane

Product 1

HCID 118276748HCID 118276748, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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. customto give a yellow solution
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo
  4. customThe crude material was purified by flash chromatography (silica gel, 40 g, 5% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1e01613364194a348b4266eae8d3d4c1
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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