Hydrochloric Acid → 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

HRID 2163137Notes

Reaction equation

HRID 2163137 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(O)[CH2:4][CH2:3]1.Cl>>[CH3:1][N:2]1[CH2:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 786701-Methyl-4-phenylpiperidin-4-ol

Product 1

HCID 13881-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine

Conditions

Temperature
100 °C

Procedure

A solution of 1-methyl-4-phenyl-4-piperidinol (60.0 g, 0.314 moles, described in Example 1) in concentrated hydrochloric acid (180 ml, 2.16 moles) is heated with stirring at 100° C. for 4 hours. The resulting brown solution is evaporated to dryness and the buff residue is crystallized from isopropanol to give the title compound as the hydrochloride salt, mp 250°-252° C. (S. M. Elvain and J. C. Safranski, Jr., supra, reported mp 248°-250° C.

Workup

  1. customThe resulting brown solution is evaporated to dryness
  2. customthe buff residue is crystallized from isopropanol

Sources & evidence

ORD record
ord-5e13418eed014748b517723bd7e8bed1
Source dataset
uspto-grants-1979_01
Patent number
US04132710

Reaction notes

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