Tryptamine → HCID 53654476, compound

HRID 1458343Notes

Reaction equation

HRID 1458343 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH2:19][CH2:20][NH2:21])=[CH:16][C:15]([N+:22]([O-:24])=[O:23])=[CH:14][CH:13]=3)[CH:6]=[C:7]([CH3:9])[CH:8]=1.C(N(CC)CC)C.NC[CH2:34][C:35]1[C:43]2C(=CC=CC=2)N[CH:36]=1.[C:44]([O:47]CC)(=[O:46])C>C(Cl)Cl>[C:35]([O:47][C:44](=[O:46])[NH:21][CH2:20][CH2:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:22]([O-:24])=[O:23])[CH:16]=2)[NH:11][C:10]=1[C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([CH3:2])[CH:4]=1)([CH3:43])([CH3:36])[CH3:34]

Participants

6

Reactant 4

HCID 1150TryptamineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 22100888HCID 22100888, compound

Product 1

HCID 53654476HCID 53654476, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]-ethylamine hydrochloride salt (1 g) was suspended in dry methylene chloride (25 mL) and dry triethylamine (0.806 mL) was added and stirred for 5 minutes at room temperature. [2-(tert-butoxycarbonyloxyimino)phenylacetronitrile] (890 mg) was added in small portions over 5 minutes to the tryptamine and the reaction mixture left to stir overnight at room temperature. The reaction was partitioned between methylene chloride and 5% citric acid. The methylene chloride layer was separated and washed with brine and dried over anhydrous sodium sulfate powder. The extract was filtered and evaporated to dryness. The product was isolated by column chromatography using silica gel and an eluant of ethyl acetate and hexanes (35:65 v/v). The yield of the title compound was 1 g.

Workup

  1. waitthe reaction mixture left
  2. stirringto stir overnight at room temperature
  3. customThe reaction was partitioned between methylene chloride and 5% citric acid
  4. customThe methylene chloride layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate powder
  7. filtrationThe extract was filtered
  8. customevaporated to dryness
  9. customThe product was isolated by column chromatography

Sources & evidence

ORD record
ord-0d25255424a148b9a25192ee9aae774a
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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