Tryptamine → HCID 20299769, compound

HRID 1733499Notes

Reaction equation

HRID 1733499 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22](O)=[O:23])[CH:18]=[CH:19][CH:20]=1>C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22]([NH:1][CH2:2][CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)=[O:23])[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 1150TryptamineHCID 15719(3-Methoxyphenyl)acetic acid

Product 1

HCID 20299769HCID 20299769, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 29 g of tryptamine and 30 g of 3-methoxy-phenylacetic acid was heated at 200° C. for one hour and after cooling the mixture to 50° C., the mixture was dissolved in 200 ml of ethyl acetate. The organic phase was washed successively with N hydrochloric acid, with water, with 2 N sodium hydroxide and with water and was dried and evaporated to dryness. The 59 g of red oil were crystallized from ether and the mixture was vacuum filtered. The product was dried to obtain 47.2 g of 3-methoxy-N-[2-(1H-indol-3-yl)-ethyl]-benzeneacetamide in the form of a beige solid melting at 78° C. which was used as is for the next step. A sample recrystallized from ether melted at 82° C.

Workup

  1. temperatureafter cooling the mixture to 50° C.
  2. washThe organic phase was washed successively with N hydrochloric acid, with water, with 2 N sodium hydroxide and with water
  3. customwas dried
  4. customevaporated to dryness
  5. customThe 59 g of red oil were crystallized from ether
  6. filtrationfiltered
  7. customThe product was dried

Sources & evidence

ORD record
ord-f0ab3d9f6ac540e7b309e9b0ed2f160a
Source dataset
uspto-grants-1980_12
Patent number
US04242355

Reaction notes

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