1,4-Dibromobutane → 6-(1-Pyrrolidinyl)-beta-carboline-3-carboxylic-acid-ethylester

HRID 1903121Notes

Reaction equation

HRID 1903121 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]([NH2:19])=[CH:13][CH:12]=3)=[O:5])[CH3:2].C(N(C(C)C)C(C)C)C.Br[CH2:30][CH2:31][CH2:32][CH2:33]Br>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]1[CH2:33][CH2:32][CH2:31][CH2:30]1)=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 80561,4-Dibromobutane2×HCID 81531DiisopropylethylamineHCID 603089Ethyl 6-amino-9H-beta-carboline-3-carboxylate

Product 1

HCID 131362526-(1-Pyrrolidinyl)-beta-carboline-3-carboxylic-acid-ethylester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

383 mg of 6-amino-beta-carboline-3-carboxylic-acid-ethylester in 15 ml of ethanol is heated together with 0.58 ml of ethyldiisopropylamine and 0.18 ml of 1,4-dibromobutane for 6 h under nitrogen at the reflux. This is followed by an addition of 0.4 ml of 1,4-dibromobutane and reflux for 3 h. After evaporation, the mixture is washed with water and boiled with ethanol. 128 mg of 6-(1-pyrrolidinyl)-beta-carboline-3-carboxylic-acid-ethylester with a m.p. of 259°-261° C. is obtained.

Workup

  1. temperaturereflux for 3 h
  2. customAfter evaporation
  3. washthe mixture is washed with water

Sources & evidence

ORD record
ord-a84434b41cde4f079404c58987c00380
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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