Thionyl Chloride → HCID 54560591, compound

HRID 2417262Notes

Reaction equation

HRID 2417262 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17]O)=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:21])=O>C1COCC1>[Cl:21][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22633982HCID 22633982, compound

Product 1

HCID 54560591HCID 54560591, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(2-Piperidin-1-yl-ethoxy)-phenyl]-ethanol (4.23 g, 16.98 mmol) was dissolved in 200 ml of THF. HCl gas was bubbled through the solution at 0° C. for 5 minutes. Still at 0° C. the thionyl chloride (2.48 ml, 33.9 mmol) was added dropwise. The reaction mixture was heated at reflux for 2 hours before it was concentrated. 1-{2-[4-(Chloro-ethyl)-phenoxy]-ethyl}-piperidine (4.74 g, 15.6 mmol) was isolated as a brown semisolid; Yield 92%; MS: 268.3 (M+H)+

Workup

  1. customHCl gas was bubbled through the solution at 0° C. for 5 minutes
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 2 hours before it
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-ad8d370f18904ece8d9a0df08c58fab5
Source dataset
uspto-grants-2004_11
Patent number
US06825354B2

Reaction notes

Loading…