Dimethylformamide → HCID 90133858, compound

HRID 1051390Notes

Reaction equation

HRID 1051390 reaction equation
CS(O[CH2:6][CH:7]([CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[CH2:14]1)[C:8]([F:11])([F:10])[F:9])(=O)=O.[C-]#N.[Na+].[CH3:32][N:33](C=O)C>CCOCC>[F:9][C:8]([F:11])([F:10])[CH:7]([CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[CH2:14]1)[CH2:6][C:32]#[N:33]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 90133853HCID 90133853, compound

Product 1

HCID 90133858HCID 90133858, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

In a 20 mL round-bottomed flask, 3,3,3-trifluoro-2-((2-(3-(trifluoromethyl)phenyl)morpholino)-methyl)propyl methanesulfonate (850 mg, 1.95 mmol) and sodium cyanide (957 mg, 19.5 mmol) were combined with DMF (30 ml) to give a light yellow solution. The reaction mixture was heated at 60° C. and stirred for 2 h. The reaction mixture was diluted with ether (60 ml), washed with brine and H2O, dried over MgSO4, filtered and concentrated to give crude product as an oil. The crude material was purified by flash chromatography (silica gel, 40 g, 0% to 60% ethyl acetate in hexanes) to afford 400 mg (56%) of 4,4,4-trifluoro-3-[2-(3-trifluoromethylphenyl)-morpholin-4-ylmethyl]-butyronitrile as a colorless oil. MH+=367.

Workup

  1. customto give a light yellow solution
  2. washwashed with brine and H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product as an oil
  7. customThe crude material was purified by flash chromatography (silica gel, 40 g, 0% to 60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-52f00d665fc94901bc9e526214a68cdf
Source dataset
uspto-grants-2016_07
Patent number
US09388172B2

Reaction notes

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