Water → 1-Methyl-3-bromo-4-phenyl-4-piperidinol

HRID 2163138Notes

Reaction equation

HRID 2163138 reaction equation
[BrH:1].[CH3:2][N:3]1[CH2:8][CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[Br-].[Na+].BrBr.[OH2:19]>>[CH3:2][N:3]1[CH2:4][CH2:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([OH:19])[CH:7]([Br:1])[CH2:8]1

Participants

5

Reactant 4

HCID 962Water2×HCID 24408BromineHCID 253881Sodium BromideHCID 227539381-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrobromide

Product 1

HCID 4350781-Methyl-3-bromo-4-phenyl-4-piperidinol

Procedure

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrobromide (110.0 g, 0.434 mole, described in Example 3) is dissolved in water (1250 ml). A solution of sodium bromide (128.0 g, 1.24 moles) and bromine (70.0 g, 0.440 mole) in water (1000 ml) is added dropwise with stirring to the above solution over a period of 1 hour. The mixture is concentrated under reduced pressure to half its original volume. The precipitate is isolated by filtration and recrystallized from glacial acetic acid to give the title compound as the hydrobromide salt, mp 191°-192° C. (R. E. Lyle and W. E. Krueger, supra, reported mp 195°-197° C.).

Workup

  1. concentrationThe mixture is concentrated under reduced pressure to half its original volume
  2. customThe precipitate is isolated by filtration
  3. customrecrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-47486d1066e741d7970cf6ce3c36e4b4
Source dataset
uspto-grants-1979_01
Patent number
US04132710

Reaction notes

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