Thionyl Chloride → 3-Pyrrolidin-1-ylmethyl-benzoyl chloride hydrochloride

HRID 1256633Notes

Reaction equation

HRID 1256633 reaction equation
[ClH:1].[N:2]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11](O)=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)([Cl:19])=O>O1CCCC1>[ClH:19].[N:2]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([Cl:1])=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 185258743-[(Pyrrolidin-1-yl)methyl]benzoic acid hydrochloride

Product 1

HCID 866594603-Pyrrolidin-1-ylmethyl-benzoyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3-pyrrolidin-1-ylmethyl-benzoic acid hydrochloride (850 mg, 3.5 mmol) in dry tetrahydrofuran was treated with 2.55 mL of thionyl chloride (35 mmol, 10 eq) and stirred at room temperature for 2 hours. The solution thus obtained was then evaporated to dryness, the residue suspended in dry toluene, evaporated to dryness and dried under vacuum affording the title compound as pale brown solid (quantitative).

Workup

  1. customThe solution thus obtained
  2. customwas then evaporated to dryness
  3. customevaporated to dryness
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f80cf0c6d3fd4e84802ff117c8cf085f
Source dataset
uspto-grants-2013_06
Patent number
US08461193B2

Reaction notes

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