1,3-Propanedithiol → 2-[4-[2-(1-Piperdinyl)ethoxy]phenyl]1,3-dithiane

HRID 1604397Notes

Reaction equation

HRID 1604397 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]([SH:22])[CH2:19][CH2:20][SH:21]>C(Cl)(Cl)Cl>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]3[S:22][CH2:18][CH2:19][CH2:20][S:21]3)=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 80131,3-PropanedithiolHCID 111838924-(2-(Piperidin-1-yl)ethoxy)benzaldehyde

Product 1

HCID 158875802-[4-[2-(1-Piperdinyl)ethoxy]phenyl]1,3-dithianeYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL, 3-neck round bottom flask was charged with 4-[2-(1-piperdinyl)ethoxy]benzaldehyde (2.3 g, 10.0 mmol) and 1,3-propanedithiol (1.2 mL, 1.1 g, 10.2 mmol) in 250 mL of anhydrous chloroform under a nitrogen atmosphere. The solution was cooled to near 0° C. and dry HBr gas was slowly bubbled through the reaction mixture for 8 minutes. The mixture was allowed to warm to ambient temperature while stirring during 3.5 hr. The reaction mixture was then added to a large excess of 1N NaOH and ice and the chloroform layer was separated. The chloroform solution was washed with two 50 mL portions of 1N NaOH solution and two 25 mL portions of brine and dried over anhydrous sodium sulfate. After filtration and removal of the chloroform solvent, the residue was triturated with 1:1 hexane:ethyl ether to provide 2.19 g (68%) of a crystalline product which was used without further purification.

Workup

  1. customdry HBr gas was slowly bubbled through the reaction mixture for 8 minutes
  2. temperatureto warm to ambient temperature
  3. additionThe reaction mixture was then added to a large excess of 1N NaOH and ice
  4. customthe chloroform layer was separated
  5. washThe chloroform solution was washed with two 50 mL portions of 1N NaOH solution and two 25 mL portions of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration and removal of the chloroform solvent
  8. customthe residue was triturated with 1:1 hexane

Sources & evidence

ORD record
ord-ecde9fe9c6d94dc78eacb281bfa81665
Source dataset
uspto-grants-1999_11
Patent number
US05994370

Reaction notes

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