Hydrochloric Acid → 2-Thiophenemethanamine, N,N-dimethyl-alpha-ethyl-alpha-(3-(3,4,5-trimethoxyphenyl)propyl)-

HRID 1708967Notes

Reaction equation

HRID 1708967 reaction equation
[CH2:1]([C:3]([NH:24][CH3:25])([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)[CH3:2].C=O.[C:28]([BH3-])#N.[Na+].Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CO>[CH2:1]([C:3]([N:24]([CH3:28])[CH3:25])([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=1)[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 106424791-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)-N-methylbutylamine

Product 1

HCID 30783212-Thiophenemethanamine, N,N-dimethyl-alpha-ethyl-alpha-(3-(3,4,5-trimethoxyphenyl)propyl)-Yield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

1.7 g of 1-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)-N-methylbutylamine are dissolved in 15 ml of acetonitrile. 1.5 ml of 35% formalin and 0.59 g of sodium cyanoborohydride are added to the solution, and the mixture is adjusted to pH 6.5 with methanol containing hydrogen chloride and stirred at room temperature for 8 hours. After the reaction, the mixture is acidified with 10% hydrochloric acid and stirred for 30 minutes. The mixture is alkalized with an aqueous 20% potassium carbonate solution and concentrated under reduced pressure. The residue is extracted with ethyl acetate, and 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; chloroform:ethanol=30:1) to give 1.4 g of 1-ethyl-4-(3,4,5-trimethoxyphenyl)-1-(2-thienyl)-N,N-dimethylbutylamine as colorless crystals. yield; 79.3% M.p. 62°-63 ° C. (recrystallized from ether-n-hexane)

Workup

  1. customAfter the reaction
  2. stirringstirred for 30 minutes
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue is extracted with ethyl acetate
  5. washthe extract is washed with an aqueous saturated sodium chloride solution
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue is purified by silica gel column chromatography (solvent; chloroform:ethanol=30:1)

Sources & evidence

ORD record
ord-75a7d2a9796d418dbfa381361c9f087a
Source dataset
uspto-grants-1990_08
Patent number
US04946862

Reaction notes

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