2-Chloro-4-[(1-cyclobutyl-4-piperidinyl)oxy]benzoic acid hydrochloride → 2-Chloro-4-[(1-cyclobutyl-4-piperidinyl)oxy]benzoyl chloride hydrochloride

HRID 268727Notes

Reaction equation

HRID 268727 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:22][CH2:21][CH2:20]3)[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6]>S(Cl)(Cl)=O>[ClH:2].[Cl:2][C:3]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:22][CH2:21][CH2:20]3)[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:4]=1[C:5]([Cl:1])=[O:6]

Participants

3

Reactant 1

HCID 689660102-Chloro-4-[(1-cyclobutyl-4-piperidinyl)oxy]benzoic acid hydrochloride

Product 1

HCID 179862522-Chloro-4-[(1-cyclobutyl-4-piperidinyl)oxy]benzoyl chloride hydrochlorideYield 199.4%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

2-Chloro-4-[(1-cyclobutyl-4-piperidinyl)oxy]benzoic acid hydrochloride (D35) (0.20 g) was dissolved in thionyl chloride (10 ml) and heated under reflux for 1.5 h. The thionyl chloride was removed by evaporation and the residue evaporated from DCM (3×10 ml) to give the title compound (D36) (0.21 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 h
  3. customThe thionyl chloride was removed by evaporation
  4. customthe residue evaporated from DCM (3×10 ml)

Sources & evidence

ORD record
ord-c5f30595da3345ba8bea3dcbfe2d3aee
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

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