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Hydrochloric Acid → 2-(2-Chloroethyl)piperidine--hydrogen chloride (1/1)

HRID 2119138
Notes
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Reaction equation

HRID 2119138 reaction equation
O[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][NH:5]1.[ClH:10]>>[ClH:10].[Cl:10][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][NH:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 151442-Piperidin-2-ylethanol

Product 1

HCID 137788862-(2-Chloroethyl)piperidine--hydrogen chloride (1/1)Yield 46%

Procedure

A 27.2 g (0.2 mole) sample of 2-(2-hydroxyethyl)piperidine was treated with ethereal hydrogen chloride and the salt was dried briefly. The solid was dissolved in 125 mL of warm chloroform and then 33.5 mL (0.46) of thionyl chloride was added in portions to the solution. The mixture was refluxed for 2.5 hr. The reaction mixture was cooled to room temperature, and the solvent evaporated in vacuo to a brown solid. The solid was recrystallized from ethanol-ether to give 17 g (46% yield) of the title compound as solid, mp=160°-162° C.

Workup

  1. customthe salt was dried briefly
  2. dissolutionThe solid was dissolved in 125 mL of warm chloroform
  3. addition33.5 mL (0.46) of thionyl chloride was added in portions to the solution
  4. temperatureThe mixture was refluxed for 2.5 hr
  5. customthe solvent evaporated in vacuo to a brown solid
  6. customThe solid was recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-e1860fa00b104be2bf3a6566ba3bcca4
Source dataset
uspto-grants-1987_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04683239

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes