Hydrochloric Acid → 1-(3,4,5-trimethoxybenzyl)-1-(2-thienyl)-N,N-dimethylpropylamine

HRID 1708969Notes

Reaction equation

HRID 1708969 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH2:6][C:7]([N+:15]#[C-:16])([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[CH2:8][CH3:9].Cl.[C:25](=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH2:6][C:7]([N:15]([CH3:25])[CH3:16])([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 230390111-(3,4,5-Trimethoxybenzyl)-1-(2-thienyl)propyl isocyanide

Product 1

HCID 230390131-(3,4,5-trimethoxybenzyl)-1-(2-thienyl)-N,N-dimethylpropylamineYield 46.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.7 g of 1-(3,4,5-trimethoxybenzyl)-1-(2-thienyl)propyl isocyanide are dissolved in 40 ml of methanol, and 5 ml of conc. hydrochloric acid are added to the solution. The mixture is stirred at 50°-60° C. for 2 hours. After the reaction, the mixture is evaporated to remove solvent and the residue (i.e., crude 1-(3,4,5-trimethoxybenzyl)-1-(2-thienyl)propylamine hydrochloride) is dissolved in a mixture of 30 ml of methanol and 2.5 g of 35% formalin. 1.84 g of sodium cyanoborohydride are added to the solution and the mixture is stirred at room temperature for 3 hours. After the reaction, the mixture is evaporated to remove solvent and 10% hydrochloric acid is added to the residue. The mixture is stirred for 15 minutes. After the reaction, the mixture is alkalized with potassium carbonate and extracted with ethyl acetate. The extract is washed with an aqueous saturated sodium chloride solution, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=2:1) to give 1.8 g of 1-(3,4,5-trimethoxybenzyl)-1-(2-thienyl)-N,N-dimethylpropylamine as a colorless oil. yield; 46.2%

Workup

  1. customAfter the reaction
  2. customthe mixture is evaporated
  3. customto remove solvent
  4. dissolutionthe residue (i.e., crude 1-(3,4,5-trimethoxybenzyl)-1-(2-thienyl)propylamine hydrochloride) is dissolved in a mixture of 30 ml of methanol and 2.5 g of 35% formalin
  5. addition1.84 g of sodium cyanoborohydride are added to the solution
  6. stirringthe mixture is stirred at room temperature for 3 hours
  7. customAfter the reaction
  8. customthe mixture is evaporated
  9. customto remove solvent and 10% hydrochloric acid
  10. additionis added to the residue
  11. stirringThe mixture is stirred for 15 minutes
  12. customAfter the reaction
  13. extractionextracted with ethyl acetate
  14. washThe extract is washed with an aqueous saturated sodium chloride solution
  15. customdried
  16. customevaporated
  17. customto remove solvent
  18. customThe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a5588f78a8034a3b951ed76eee4cb118
Source dataset
uspto-grants-1990_08
Patent number
US04946862

Reaction notes

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