Allyl bromide → HCID 20148438, compound

HRID 569040Notes

Reaction equation

HRID 569040 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[CH2:15](Br)[CH:16]=[CH2:17].[C:19]1([C:30]2CCCCCCCCCC=2)[CH2:29]CCCCCCCNN=1>C(O)C>[CH2:15]([N:1]([CH2:30][CH:19]=[CH2:29])[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1)[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 3172186453-27-6HCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 20148438HCID 20148438, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

360 mg of 6-amino-β-carboline are heated in 20 ml of ethanol with 0.54 ml of allylbromide and 0.74 ml diazabicycloundecene for 3 hours at 70° C. After concentration to dryness and dispersing in ethyl acetate/saturated sodium chloride solution, the organic phase is separated, dried, filtered and concentrated. The residue is chromatographed on silica gel with cyclohexane/ethyl acetate=1:1 as eluant and 50 mg of 6-diallylamino-β-carboline as oil are obtained.

Workup

  1. concentrationAfter concentration to dryness
  2. additiondispersing in ethyl acetate/saturated sodium chloride solution
  3. customthe organic phase is separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel with cyclohexane/ethyl acetate=1:1 as eluant

Sources & evidence

ORD record
ord-655dcb9f534a47d783a1c71e79b928d1
Source dataset
uspto-grants-1988_03
Patent number
US04731358

Reaction notes

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