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

HRID 66320Notes

Reaction equation

HRID 66320 reaction equation
[Cl:1][CH2:2][CH:3]([OH:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH2:18][CH2:19][NH2:20].C(Cl)(Cl)Cl.Cl>C(O)C.C(OCC)C>[ClH:1].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH2:18][CH2:19][NH:20][CH2:2][CH:3]([OH:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 8421HomoveratrylamineHCID 224917592-Chloro-1-(2-methoxyphenyl)ethan-1-ol

Product 1

HCID 22754925alpha-(3,4-Dimethoxyphenethylaminomethyl)-2-methoxybenzylalcohol hydrochlorideYield 41.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.7 g of α-chloromethyl-2-methoxybenzylalcohol (crude oil) and 10.9 g 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. 30 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. 3.0 g 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. addition30 ml of ethanol are added to the residue
  8. customobtained
  9. customcrystalline precipitates
  10. filtrationare collected by filtration

Sources & evidence

ORD record
ord-fe01ba9c7d884a63b445b6e999ea679e
Source dataset
uspto-grants-1978_12
Patent number
US04131686

Reaction notes

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