Hydrochloric Acid → HCID 20374242, compound

HRID 1834148Notes

Reaction equation

HRID 1834148 reaction equation
O[CH2:2][CH2:3][N:4]1[CH2:11][CH2:10][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:8]#[N:9])[CH2:6][CH2:5]1.[ClH:18].S(Cl)([Cl:21])=O>C(Cl)Cl>[ClH:21].[Cl:18][CH2:2][CH2:3][N:4]1[CH2:11][CH2:10][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:8]#[N:9])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 20374276HCID 20374276, compound

Product 1

HCID 20374242HCID 20374242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution is prepared from 5.9 parts of the nitrile obtained in the preceding paragraph and 134 parts of methylene chloride. This solution is saturated with hydrogen chloride gas at below 10° C. and 5.1 parts of thionyl chloride is added. The mixture is refluxed for 1 hour and then cooled and volatile material is removed under reduced pressure. The residue is dissolved in 88 parts of benzene, and the solution evaporated under reduced pressure. The residue is then crystallized from a mixture of ethanol and ether to give 1-(2-chloroethyl)-4-phenylisonipecotonitrile hydrochloride.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. temperaturecooled
  3. customvolatile material is removed under reduced pressure
  4. dissolutionThe residue is dissolved in 88 parts of benzene
  5. customthe solution evaporated under reduced pressure
  6. customThe residue is then crystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-34dade4b78dd4b3e81d89faee6a421bb
Source dataset
uspto-grants-1978_01
Patent number
US04069223

Reaction notes

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