1,5-Dibromopentane → HCID 20148416, compound

HRID 569030Notes

Reaction equation

HRID 569030 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>O1CCCC1.C(O)C>[N:1]1([C:2]2[N:3]=[CH:4][C:5]3[NH:6][C:7]4[C:12]([C:13]=3[CH:14]=2)=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 81001,5-DibromopentaneHCID 1195373-AminonorharmanHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 20148416HCID 20148416, compoundYield 6.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

549 mg of 3-amino-β-carboline are refluxed for 4 hours with 1.5 g of 1,5-dibromopentane and 1 g of diazabicycloundecene in 25 ml of tetrahydrofuran and 5 ml of absolute ethanol. After evaporation, the product is chromatographed on silica gel with cyclohexane/ethyl acetate=1:1 as eluant. 50 mg of 3-piperidino-β-carboline are obtained as oil.

Workup

  1. customAfter evaporation
  2. customthe product is chromatographed on silica gel with cyclohexane/ethyl acetate=1:1 as eluant

Sources & evidence

ORD record
ord-f3ca17ebbfb940d8aef9bbcfbb951d68
Source dataset
uspto-grants-1988_03
Patent number
US04731358

Reaction notes

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