Tryptamine → HCID 4780352, compound

HRID 883441Notes

Reaction equation

HRID 883441 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.BrC1C=CC(F)=C([N+]([O-])=O)C=1.F[C:25]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][C:26]=1[C:27]#[N:28].ClCCl>C(O)C.C(OCC)C>[C:27]([C:26]1[CH:29]=[C:30]([N+:33]([O-:35])=[O:34])[CH:31]=[CH:32][C:25]=1[NH: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)#[N:28]

Participants

7

Reactant 4

HCID 1150TryptamineHCID 6344DichloromethaneHCID 5194172-Fluoro-5-nitrobenzonitrileHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 4780352HCID 4780352, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

2×500 mg (2×1 equiv) of tryptamine were dissolved under an argon atmosphere in 2×2 ml of absolute ethanol in three different flasks of a Carousel parallel synthesizer. 4-bromo-1-fluoro-2-nitrobenzene (690 mg, 1 equiv) and 2-fluoro-5-nitrobenzonitrile (520 mg, 1 equiv) were added, respectively, in one of the two parallel flasks (A and B) and the obtained mixtures were allowed to react at room temperature under magnetic stirring. The course of the reactions was followed by TLC (dichloromethane as the eluent). Reactions A and B were completed after 8 and 2 hours, respectively. The two mixtures were then diluted with ca. 15 ml of diethyl ether and the resulting precipitates were collected by filtration and washed with additional Et2O. TLC analyses showed in all precipitates residual traces of starting materials, thus each reaction mixture was purified by column chromatography on silica gel (approx. 20 grams). A mixture of petroleum ether/dichloromethane (8:2) was used until the starting nitroaromatic derivatives were eluted; subsequently, the target products were eluted by using dichloromethane. N-(2-nitro-4-bromophenyl)-tryptamine was collected as a red solid in 55% yield and finally N-(2-cyano-4-nitrophenyl)-tryptamine was obtained as a yellow solid in 40% yield.

Workup

  1. customto react at room temperature under magnetic stirring
  2. customafter 8 and 2 hours
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with additional Et2O
  6. customthus each reaction mixture was purified by column chromatography on silica gel (approx. 20 grams)
  7. additionA mixture of petroleum ether/dichloromethane (8:2)
  8. washwere eluted
  9. washsubsequently, the target products were eluted
  10. customN-(2-nitro-4-bromophenyl)-tryptamine was collected as a red solid in 55% yield

Sources & evidence

ORD record
ord-b654a4d05d744221872a3eaf05151a82
Source dataset
uspto-grants-2012_08
Patent number
US08236858B2

Reaction notes

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