O-Methyltyramine → HCID 18993026, compound

HRID 846578Notes

Reaction equation

HRID 846578 reaction equation
[NH2:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8].[CH2:9](OC(OCC)OCC)C.C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][NH2:41])=[CH:35][CH:34]=1>O.C(O)(=O)C>[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][NH:41][C:7]2[C:6]3[CH:5]=[CH:4][O:3][C:2]=3[N:1]=[CH:9][N:8]=2)=[CH:35][CH:34]=1

Participants

8

Reactant 5

HCID 4657O-MethyltyramineHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 517045Sodium AcetateHCID 227196132-Amino-3-cyanofuran

Product 1

HCID 18993026HCID 18993026, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

The 2-amino-3-cyanofuran produced in the preceding step was combined with 4.2 mL of triethylorthoformate, and 0.5 mL of acetic anhydride, and the mixture was heated to 130° C. for two hours. Then was added 1.8 g of sodium acetate and 3 g of 2-(4-methoxyphenyl)ethylamine, followed by 3 mL of acetic acid. The resulting mixture was heated for two hours at 130°-138° C., then cooled and diluted with water. The product was extracted with large volumes of ether. The ether extracts were combined, washed with water, dried over magnesium sulfate, and concentrated. The residue was recrystallized from ether and petroleum ether. Yield 0.65 g. M.P. 135°-136° C.

Workup

  1. temperatureThe resulting mixture was heated for two hours at 130°-138° C.
  2. temperaturecooled
  3. extractionThe product was extracted with large volumes of ether
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ether and petroleum ether

Sources & evidence

ORD record
ord-f223448a785043349da6ddec745ebbfe
Source dataset
uspto-grants-1992_08
Patent number
US05137879

Reaction notes

Loading…