Dimethylformamide → HCID 17755403, compound

HRID 1640125Notes

Reaction equation

HRID 1640125 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[N+:9]([C:12]1[CH:13]=[C:14]([OH:22])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)([O-:11])=[O:10].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>CCOC(C)=O>[N+:9]([C:12]1[CH:13]=[C:14]([CH:15]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:17]=1)[O:22][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 816691-(2-Chloroethyl)pyrrolidineHCID 27562513-Hydroxy-5-nitrobenzotrifluoride

Product 1

HCID 17755403HCID 17755403, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(2-chloroethyl)pyrrolidine (0.355 g, 2.66 mmol), 3-nitro-5-(trifluoromethyl)phenol (0.500 g, 2.41 nmmol), Cs2CO3 (2.36 g, 7.24 mmol), and DMF (18.69 mL) was allowed to stir at rt until reaction was judged to be complete. The mixture was diluted with EtOAc and washed with water (3×25 mL). The organic solution was dried over Na2SO4, filtered, and concentrated to give 3-(2-pyrrohidin-1-ylethoxy)-5-(trifluoromethyl)anlline as a brown oil (0.49 g, 63%). LCMS: (FA) ES+ 304.3.

Workup

  1. washwashed with water (3×25 mL)
  2. dry with materialThe organic solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give 3-(2-pyrrohidin-1-ylethoxy)-5-(trifluoromethyl)anlline as a brown oil (0.49 g, 63%)

Sources & evidence

ORD record
ord-378224d8bf1f42ada0835c1687cad6a9
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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