Hydrochloric Acid → alpha-(3,4-Dimethoxyphenethylaminomethyl)-2-methoxybenzylalcohol hydrochloride

HRID 66323Notes

Reaction equation

HRID 66323 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:11][O:10]1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:17][CH2:18][NH2:19].C(Cl)(Cl)[Cl:26].Cl>C(O)C.C(OCC)C>[ClH:26].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:17][CH2:18][NH:19][CH2:11][CH:9]([OH:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 8421HomoveratrylamineHCID 113555722-(2-Methoxyphenyl)oxirane

Product 1

HCID 22754925alpha-(3,4-Dimethoxyphenethylaminomethyl)-2-methoxybenzylalcohol hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.5 g of 2-(2-methoxyphenyl)oxirane (crude product) and 600 mg of 3,4-dimethoxyphenethylamine is heated at 130° to 140° C. for 2 hours. After cooling, chloroform is added to the reaction mixture, and said mixture is washed with water. The mixture is dried and evaporated to remove solvent. 2 ml of ethanol are added to the residue obtained. Then, hydrochloric acid-containing diethylether is added to the ethanol mixture, and crystalline precipitates are collected by filtration. 290 mg of α-(3,4-dimethoxyphenethylaminomethyl)-2-methoxybenzylalcohol hydrochloride are obtained as crystals. M.p. 142°-143° C.

Workup

  1. temperatureis heated at 130° to 140° C. for 2 hours
  2. temperatureAfter cooling
  3. washis washed with water
  4. customThe mixture is dried
  5. customevaporated
  6. customto remove solvent
  7. addition2 ml of ethanol are added to the residue
  8. customobtained
  9. customcrystalline precipitates
  10. filtrationare collected by filtration

Sources & evidence

ORD record
ord-3c46bf617041418a86107e3f0c445eca
Source dataset
uspto-grants-1978_12
Patent number
US04131686

Reaction notes

Loading…