Thionyl Chloride → 3-[5-Chloro-1-(4-fluorophenyl)pentyl]pyridine

HRID 1494639Notes

Reaction equation

HRID 1494639 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:13][CH2:14][CH2:15][CH2:16]O)=[CH:8][CH:7]=1>>[Cl:3][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[C:9]1[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 14722561epsilon-(4-Fluorophenyl)-3-pyridinepentanol

Product 1

HCID 147225623-[5-Chloro-1-(4-fluorophenyl)pentyl]pyridineYield 100%

Procedure

64 Parts of thionyl chloride were added portionwise to 4 parts of ε-(4-fluorophenyl)-3-pyridinepentanol. Upon complete addition, stirring was continued for 2 hours at reflux temperature. The reaction mixture was evaporated and the residue was taken up in water. The whole was treated with sodium carbonate. The product was extracted twice with methylbenzene. The combined extracts were washed with water, dried, filtered and evaporated, yielding 3.7 parts (100%) of 3-[5-chloro-1-(4-fluorophenyl)pentyl]pyridine as a residue (int. 57).

Workup

  1. additionUpon complete addition
  2. temperatureat reflux temperature
  3. customThe reaction mixture was evaporated
  4. additionThe whole was treated with sodium carbonate
  5. extractionThe product was extracted twice with methylbenzene
  6. washThe combined extracts were washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-1b496d8aeb684e73b5919f4827c5bc1c
Source dataset
uspto-grants-1991_06
Patent number
US05026853

Reaction notes

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