3,4-Dimethoxyphenethyl bromide → HCID 19803671, compound

HRID 1682005Notes

Reaction equation

HRID 1682005 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:18][CH2:19]Br)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]>C(N(CC)CC)C.C(Cl)Cl.[OH-].[Na+]>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:18][CH2:19][N:5]2[CH2:6][CH2:7][CH:3]([CH2:2][OH:1])[CH2:4]2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

6

Reactant 2

HCID 114706023,4-Dimethoxyphenethyl bromideHCID 13400657(Pyrrolidin-3-yl)methanol

Product 1

HCID 19803671HCID 19803671, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 14798Sodium HydroxideSolvent

Procedure

3 g (0.03 mol) of 3-hydroxymethyl-pyrrolidine and 7.5 g of 2-(3,4-dimethoxy-phenyl)-ethylbromide are heated in 20 ml of triethylamine for 7 hours at 100° C. The excess triethylamine is then distilled off in vacuo and the residue obtained is dissolved in methylene chloride and 6 molar sodium hydroxide solution. The organic phase is separated off, dried over magnesium sulphate and concentrated by evaporation in vacuo. The residue obtained is then purified over 400 g of alumium oxide (neutral, activity II) with methylene chloride and with increasing amounts of ethanol (up to 1%). Yield: 5.4 g (67.8% of theory), Rf value: 0.41 (aluminium oxide, neutral, eluant: 5% ethanol in methylene chloride).

Workup

  1. distillationThe excess triethylamine is then distilled off in vacuo
  2. customthe residue obtained
  3. customThe organic phase is separated off
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. customThe residue obtained
  7. customis then purified over 400 g of alumium oxide (neutral, activity II) with methylene chloride and with increasing amounts of ethanol (up to 1%)

Sources & evidence

ORD record
ord-b1f145d571f84057822861ea1cf430dd
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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