4-Fluorobenzonitrile → HCID 12875685, compound

HRID 1065634Notes

Reaction equation

HRID 1065634 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:3].[H-].[Na+].F[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1.O.O.C(O)(=O)C(O)=O>CS(C)=O.C(OCC)(=O)C.O>[C:21]([C:20]1[CH:23]=[CH:24][C:17]([O:13][CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])=[CH:18][CH:19]=1)#[N:22]

Participants

8

Reactant 4

HCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 61373Oxalic acid dihydrateHCID 1106653-(Dimethylamino)-1-phenylpropan-1-ol

Product 1

HCID 12875685HCID 12875685, compoundYield 85.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of N,N-dimethyl-3-hydroxy-3-phenylpropylamine (3.58 g, 20 mM), 50% sodium hydride dispersion (1 g) and DMSO (50 ml) was heated at 80° until homogenous, cooled to ambient temperature and treated dropwise with a solution of 4-fluorobenzonitrile (2.42 g, 20 mM) in DMSO with cooling (exothermic). After 1 h the reaction mixture was poured on to water (200 ml) and extracted with ether (2×200 ml). The ether extract was extracted with 1 N hydrochloric acid (2×50 ml), the acid extract basified and then extracted with ether (2×200 ml). The ether was dried and the solvents removed under reduced pressure to give an oil which was dissolved in ethyl acetate and treated with an excess of a solution of oxalic acid dihydrate in ethyl acetate. Removal of the resultant precipitate by filtration followed by recrystallisation from ethyl acetate gave the title compound (4.8 g) as the oxalate quarter hydrate m.p. 80° (decomp). Found: C, 64.1; H, 6.05; N, 7.7% C18H20N2O.C2H2O4 requires: C, 64.1; H, 6.1; N 7.5%.

Workup

  1. temperaturewas heated at 80° until homogenous,
  2. temperaturewith cooling (exothermic)
  3. extractionextracted with ether (2×200 ml)
  4. extractionThe ether extract
  5. extractionwas extracted with 1 N hydrochloric acid (2×50 ml)
  6. extractionthe acid extract
  7. extractionextracted with ether (2×200 ml)
  8. dry with materialThe ether was dried
  9. customthe solvents removed under reduced pressure
  10. customto give an oil which
  11. customRemoval of the resultant precipitate
  12. filtrationby filtration
  13. customfollowed by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-1633a8b3d84c4cf994a9182678e1d234
Source dataset
uspto-grants-1982_05
Patent number
US04330546

Reaction notes

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