Hydrochloric Acid → HCID 70619308, compound

HRID 1833372Notes

Reaction equation

HRID 1833372 reaction equation
O[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1.[ClH:21].S(Cl)([Cl:24])=O>C(Cl)Cl>[ClH:24].[CH2:13]([O:12][C:10]([C:7]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][Cl:21])[CH2:5][CH2:6]1)=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 21389218Ethyl 1-(2-hydroxyethyl)-4-phenylpiperidine-4-carboxylate

Product 1

HCID 70619308HCID 70619308, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution is prepared from 5.9 parts of the ester obtained in the preceding paragraph and 134 parts of methylene chloride. This solution is saturated with hydrogen chloride gas at below 10° 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-phenyl-4-piperidinecarboxylic acid ethyl ester hydrochloride melting at about 216°-218°.

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-5379cecf792146e5b5fae09dc1df67b9
Source dataset
uspto-grants-1978_01
Patent number
US04066654

Reaction notes

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