Sodium hydride → HCID 12951847, compound

HRID 1248797Notes

Reaction equation

HRID 1248797 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH2:8][N:9]([CH2:11][CH2:12][CH:13]([OH:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:10])[CH:7]=1.[H-].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:20][CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][N:9]([CH3:10])[CH2:8][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 12951849HCID 12951849, compound

Product 1

HCID 12951847HCID 12951847, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of N-(5-chloro-2-fluorophenyl)methyl-N-methyl-3-hydroxy-3-phenylpropylamine (3.1 g), 50% sodium hydride dispersion (480 mg) and DMSO (100 ml) was maintained at 50° under nitrogen for 12 h. The mixture was poured onto water (500 ml) and extracted with ether (3×300 ml) The combined organic extracts were washed, dried and evaporated. Chromatography of the residue on silica (Woelm Grade 1) using ethyl acetate as eluant gave the title compound (1.6 g). This was converted to the tosylate in ether/IPA, m.p. 219°-221°.

Workup

  1. temperaturewas maintained at 50° under nitrogen for 12 h
  2. additionThe mixture was poured onto water (500 ml)
  3. extractionextracted with ether (3×300 ml) The combined organic extracts
  4. washwere washed
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-9a70e9e8169a43878595e115d62c86d9
Source dataset
uspto-grants-1986_12
Patent number
US04626522

Reaction notes

Loading…