Triethylamine → HCID 13288304, compound

HRID 1681995Notes

Reaction equation

HRID 1681995 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH2:26][CH2:27]Br)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]>[OH-].[Na+].C(Cl)Cl>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH2:26][CH2:27][N:5]2[CH2:6][CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4]2)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 107308Piperidin-3-ylmethanolHCID 114706023,4-Dimethoxyphenethyl bromide

Product 1

HCID 13288304HCID 13288304, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2.30 g (0.02 mol) of 3-(hydroxymethyl)piperidine, 5.5 ml (0.04 mol) of triethylamine and 4.90 g (0.02 mol) of 2-(3,4-dimethoxy-phenyl)-ethyl bromide is refluxed for 2 hours. After cooling, the reaction mixture is dissolved in a mixture of 2 molar sodium hydroxide solution and methylene chloride. The organic phase is washed with water, separated off, dried over magnesium sulphate, evaporated down in vacuo and purified over 300 g of aluminium oxide (neutral, activity II-III) with methylene chloride and then with increasing amounts of ethanol (up to 2%). Yield: 4.4 g (78.7% of theory), Melting point: 87.5°-89° C.

Workup

  1. temperatureis refluxed for 2 hours
  2. temperatureAfter cooling
  3. washThe organic phase is washed with water
  4. customseparated off
  5. dry with materialdried over magnesium sulphate
  6. customevaporated down in vacuo
  7. custompurified over 300 g of aluminium oxide (neutral, activity II-III) with methylene chloride

Sources & evidence

ORD record
ord-60554666bc74477dbccb2390c9e90b76
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

Loading…