Thionyl Chloride → HCID 19857186, compound

HRID 2073497Notes

Reaction equation

HRID 2073497 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23]O)[CH2:18][CH2:17]2)=[CH:8][CH:7]=1>C(Cl)Cl>[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][Cl:3])[CH2:18][CH2:17]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19857170HCID 19857170, compound

Product 1

HCID 19857186HCID 19857186, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

115 g of thionyl chloride were added dropwise to 23 g (61.6 mmol) of 1-[4,4-bis(4-fluorophenyl)butyl]-4-(2-hydroxyethyl)piperidine in 100 ml of methylene chloride, while cooling with ice, and the mixture was then heated under reflux for 5.5 hours. The solvent and excess reagent were stripped off in vacuo, the residue (the hydrochloride of the product) was crystallized by addition of 450 ml of ether and the crystals were filtered off with suction, washed several times with ether and dried in vacuo.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturethe mixture was then heated
  3. temperatureunder reflux for 5.5 hours
  4. customthe residue (the hydrochloride of the product) was crystallized by addition of 450 ml of ether
  5. filtrationthe crystals were filtered off with suction
  6. washwashed several times with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7e1b79e46266431699ef19b0ea293cbd
Source dataset
uspto-grants-1990_04
Patent number
US04918073

Reaction notes

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