Water → HCID 19803750, compound

HRID 1681996Notes

Reaction equation

HRID 1681996 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19]O)[CH2:14]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Br)(Br)[Br:22].O.[OH-].[Na+]>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][Br:22])[CH2:14]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 13288304HCID 13288304, compound

Product 1

HCID 19803750HCID 19803750, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

4.4 g (0.0157 mol) of N-[2-(3,4-dimethoxy-phenyl)-ethyl]-3(hydroxymethyl)-piperidine are dissolved in 70 ml of carbon tetrachloride and cooled to 0° C. Then 1.63 ml (0.0173 mol) of phosphorus tribromide is added, whereupon a bulky precipitate is immediately formed. The mixture is stirred for 15 hours at ambient temperature, water is added and the mixture is neutralized with 2 molar sodium hydroxide solution. The organic phase is separated off, washed with water, dried over magnesium sulphate, concentrated by evaporation in vacuo and purified over 310 g of aluminium oxide (neutral, activity II-III) with methylene chloride and then with increasing amounts of ethanol (up to 5%). Yield: 2.0 g (37.2% of theory), Rf value: 0.5 (aluminium oxide neutral, eluant: 2% ethanol in methylene chloride).

Workup

  1. customis immediately formed
  2. customThe organic phase is separated off
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. custompurified over 310 g of aluminium oxide (neutral, activity II-III) with methylene chloride

Sources & evidence

ORD record
ord-f8a11ebd0d4341b9967025536ebbc899
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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