Benzyl Chloride → HCID 18928788, compound

HRID 1681989Notes

Reaction equation

HRID 1681989 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:9](N(CC)CC)C.[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-:24].[Na+]>C(OCC)(=O)C>[CH2:16]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([CH2:2][CH2:9][OH:24])[CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 18928788HCID 18928788, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 40.3 g (0.35 mol) of 3-(hydroxymethyl)piperidine, 97.4 ml (0.70 mol) of triethylamine and 40.3 ml (0.35 mol) of benzyl chloride is heated to 95° C. within 30 minutes and left at this temperature for 2 hours. After cooling the reaction mixture is dissolved in a mixture of 2 molar sodium hydroxide solution and ethyl acetate. The organic phase is washed with water, separated off, dried over magnesium sulphate and concentrated by evaporation in vacuo. Yield: 57.2 g (79.6% of theory), Rf value: 0.45 (aluminium oxide neutral, eluant: 3% ethanol in methylene chloride).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. washThe organic phase is washed with water
  3. customseparated off
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-a95f1f96758a4678906fa1e1d4066389
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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