Sodium hydride → HCID 12951847, compound

HRID 2058662Notes

Reaction equation

HRID 2058662 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 dispension (480 mg) and DMSO (100 ml) was maintained at 50° under nitrogen for 12h. 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°. (Found C, 62.2; H, 5.6; N, 2.7%. C17H18ClNO. C7H8SO3 requires: C, 62.65; H, 5.7; N, 3.0%).

Workup

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

Sources & evidence

ORD record
ord-f4e8cf05104f4591b4e4b23d11f0f656
Source dataset
uspto-grants-1982_03
Patent number
US04318909

Reaction notes

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