Homoveratrylamine → 5-[N-(3,4-dimethoxyphenethyl)-2-aminoethyl]-4,5,6,7-tetrahydro-thieno-(3,2-c)-pyridine

HRID 2118956Notes

Reaction equation

HRID 2118956 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][C:7]2[S:10][CH:11]=[CH:12][C:6]=2[CH2:5]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][NH2:20]>O>[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][CH2:3][N:4]1[CH2:9][CH2:8][C:7]2[S:10][CH:11]=[CH:12][C:6]=2[CH2:5]1

Participants

4

Reactant 2

HCID 8421HomoveratrylamineHCID 136332135-(2-Chloroethyl)-4,5,6,7-tetrahydro-thieno-(3,2-c)-pyridine

Product 1

HCID 136332145-[N-(3,4-dimethoxyphenethyl)-2-aminoethyl]-4,5,6,7-tetrahydro-thieno-(3,2-c)-pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Into a two liter reactor, fitted with an oil-bath and stirring means and under nitrogen circulation, were poured 201.5 g (1 mol) of 5-(2-chloroethyl)-4,5,6,7-tetrahydro-thieno-(3,2-c)-pyridine and slowly, under stirring, 181 g (1 mol) of 3,4-dimethoxyphenethylamine. The reacting mixture was warmed at 110° C. under stirring for two hours. The oily mixture obtained was cooled to about 70°-80° C. and then poured into icy water; after separation, washing, extraction with diethyl ether and drying, the residue was dissolved in a mixture of petroleum ether and isopropyl ether (50/50 by volume) and passed through a silica gel column. Elution was with acetone. The fraction containing the desired compound was evaporated to dryness, treated with diethyl ether and finally with acetone. Yield 163 g (47%) of a white crystalline powder soluble in water, melting at 260° C. (Tottoli) with decomposition, the analysis and NMR of which showed a good correspondence with the formula C19H26N2O2S.

Workup

  1. customInto a two liter reactor, fitted with an oil-bath
  2. stirringslowly, under stirring
  3. stirringunder stirring for two hours
  4. customThe oily mixture obtained
  5. temperaturewas cooled to about 70°-80° C.
  6. customafter separation
  7. washwashing
  8. extractionextraction with diethyl ether
  9. customdrying
  10. dissolutionthe residue was dissolved in a mixture of petroleum ether and isopropyl ether (50/50 by volume)
  11. washElution
  12. additionThe fraction containing the desired compound
  13. customwas evaporated to dryness
  14. additiontreated with diethyl ether and finally with acetone

Sources & evidence

ORD record
ord-803e223c7e254ea0af5961823b88359c
Source dataset
uspto-grants-1987_07
Patent number
US04681888

Reaction notes

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