Thionyl Chloride → 4-(2-Piperidin-1-ylethoxy)benzoyl chloride hydrochloride

HRID 1827946Notes

Reaction equation

HRID 1827946 reaction equation
[ClH:1].[N:2]1([CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)([Cl:22])=O>>[ClH:22].[N:2]1([CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([Cl:1])=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 57438354-(2-Piperidinoethoxy)benzoic acid hydrochloride

Product 1

HCID 161119224-(2-Piperidin-1-ylethoxy)benzoyl chloride hydrochloride

Procedure

A 500 mL round-bottom flask is charged with 4-(2-piperidin-1-yl-ethoxy)-benzoic acid hydrochloride, (25 g, 0.08748 mol) and thionyl chloride (150 mL, 2.0564 mol). The mixture is brought to reflux for 15 minutes whereupon it becomes a clear solution. The reaction is cooled to room temperature and the excess thionyl chloride is removed to give a quantitative yield of the desired product. 1H NMR: ∂ 8.08 (app. d, J=8.8 Hz, 2H), 6.99 (app. d, J=9.2 Hz, 2H), 4.71 (t, J=4.6 Hz, 2H), 3.65 (d, J=12 Hz, 2H), 3.43 (quart., J=4.6 Hz, 2H), 2.76–2.85 (m, 2H), 2.22–2.32 (m, 2H), 1.87–1.94 (m, 3H), 1.37–1.49 (m, 1H).

Workup

  1. temperatureto reflux for 15 minutes whereupon it
  2. customthe excess thionyl chloride is removed

Sources & evidence

ORD record
ord-afbe9fcd409d456c973b27ab03942118
Source dataset
uspto-grants-2006_06
Patent number
US07056931B2

Reaction notes

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