Hydrochloric Acid → cis-1-(3-Chloropropyl)-2,6-dimethylpiperidine

HRID 1763483Notes

Reaction equation

HRID 1763483 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH3:8])[N:3]1[CH2:9][CH2:10][CH2:11]O.S(Cl)([Cl:15])=O.Cl.[OH-].[Na+]>O.CCOCC.C1C=CC=CC=1>[Cl:15][CH2:11][CH2:10][CH2:9][N:3]1[C@H:2]([CH3:1])[CH2:7][CH2:6][CH2:5][C@@H:4]1[CH3:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 13239624cis-2,6-Dimethyl-1-piperidinepropanol

Product 1

HCID 12923591cis-1-(3-Chloropropyl)-2,6-dimethylpiperidine

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of 171 g. of cis-2,6-dimethyl-1-piperidinepropanol in 400 ml. of benzene is cooled to 0°-5° and 143 g. of thionyl chloride is added dropwise over a period of 30 minutes. The mixture is then heated at reflux for 2 hours, cooled and diluted with 1 l. of ether. The resulting precipitate of cis-1-(3-chloropropyl)-2,6-dimethylpiperidine hydrochloride is collected by filtration; m.p. 173°-174° C. after crystallization from 2-propanol-ether. The free base is prepared as needed by dissolving the hydrochloride in a minimum amount of water, cooling and adding a slight excess of 50% aqueous sodium hydroxide. The liberated base is immediately extracted with several portions of benzene. The extracts are combined, dried and evaporated to give the free base, cis-1-(3-chloropropyl)-2,6-dimethylpiperidine.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. additiondiluted with 1 l
  5. filtrationThe resulting precipitate of cis-1-(3-chloropropyl)-2,6-dimethylpiperidine hydrochloride is collected by filtration
  6. customm.p. 173°-174° C. after crystallization from 2-propanol-ether
  7. customThe free base is prepared
  8. temperaturecooling
  9. extractionThe liberated base is immediately extracted with several portions of benzene
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-a3e2144749544661b218a4013504f25b
Source dataset
uspto-grants-1978_09
Patent number
US04112103

Reaction notes

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