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

HRID 66325Notes

Reaction equation

HRID 66325 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([CH:12]=O)=[O:11])[CH3:2].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:19][CH2:20][NH2:21].COC1C=C(C=CC=1OC)CCN=C(OC)C(C1C=CC=CC=1)=O.[BH4-].[Na+].[ClH:53]>C(O)C>[ClH:53].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:19][CH2:20][NH:21][CH2:12][CH:10]([OH:11])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[O:3][CH2:1][CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8421HomoveratrylamineHCID 4311764Sodium borohydrideHCID 227549162-EthoxyphenylglyoxalHCID 22754918alpha-(3,4-Dimethoxyphenethylimino)-2-methoxyacetophenone

Product 1

HCID 22754923alpha-(3,4-Dimethoxyphenethylaminomethyl)-2-ethoxybenzylalcohol hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.1 g of 2-ethoxyphenylglyoxal (crude oil) are dissolved in 20 ml of ethanol, and 1.85 g of 3,4-dimethoxyphenethylamine are added thereto. The solution is stirred at room temperature for 30 minutes, whereby a solution containing α-(3,4-dimethoxyphenethylimino)-2-methoxyacetophenone is obtained. 0.6 g of sodium borohydride is added gradually to said solution under ice-cooling, and the mixture is stirred at room temperature for one hour. The reaction mixture is evaporated to remove solvent. Water is added to the thus obtained residue. Then, the aqueous mixture is extracted with chloroform. The extract is washed with water, dried and then evaporated to remove solvent. The oily residue thus obtained is treated with hydrochloric acid and recrystallized from a mixture of isopropanol and ether. 3.1 g of α-(3,4-dimethoxyphenethylaminomethyl)-2-ethoxybenzylalcohol hydrochloride are obtained. M.p. 169°-170° C.

Workup

  1. customis obtained
  2. temperaturecooling
  3. stirringthe mixture is stirred at room temperature for one hour
  4. customThe reaction mixture is evaporated
  5. customto remove solvent
  6. additionWater is added to the thus obtained residue
  7. extractionThen, the aqueous mixture is extracted with chloroform
  8. washThe extract is washed with water
  9. customdried
  10. customevaporated
  11. customto remove solvent
  12. customThe oily residue thus obtained
  13. customrecrystallized from a mixture of isopropanol and ether

Sources & evidence

ORD record
ord-2b0ad1c9870941afaf4b6eb64c024677
Source dataset
uspto-grants-1978_12
Patent number
US04131686

Reaction notes

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