Allyl bromide → HCID 13136259, compound

HRID 1982464Notes

Reaction equation

HRID 1982464 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([NH:19][CH2:20][CH3:21])=[CH:13][CH:12]=3)=[O:5])[CH3:2].[CH:22]1(C2CCCCCCCCCC2)[CH2:32]CCCCC=CCC[CH2:23]1.C(Br)C=C>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([N:19]([CH2:32][CH:22]=[CH2:23])[CH2:20][CH3:21])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 23316472HCID 23316472, compoundHCID 131713412HCID 131713412, compound

Product 1

HCID 13136259HCID 13136259, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

93 mg of 6-(N-ethylamino)-beta-carboline-3-carboxylic-acid-ethylester in 8 ml of absolute ethanol is heated together with 49 mg of 1,5-diaza-[5.4.0]bicycloundec-5-ene and 50 mg of allyl bromide under nitrogen for 2 h at 70° C. After evaporation, the substance is distributed in ethyl acetate and saturated sodium bicarbonate solution. The organic phase is dried, filtered and concentrated. The residue is chromatographed by means of 80 g of silica gel with methylene-chloride/ethanol (12/1) as the eluant, and, after recrystallizing out of ethyl-acetate/ether, 56 mg of 6-(N-allyl-N-ethylamino)-beta-carboline-3-carboxylic-acid-ethylester is obtained (m.p. 190°-192° C.).

Workup

  1. customAfter evaporation
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is chromatographed by means of 80 g of silica gel with methylene-chloride/ethanol (12/1) as the eluant
  6. customafter recrystallizing out of ethyl-acetate/ether

Sources & evidence

ORD record
ord-b048f02385314196a741a8e60e3fcc74
Source dataset
uspto-grants-1986_06
Patent number
US04596808

Reaction notes

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