1,5-Dibromopentane → HCID 13136254, compound

HRID 1903123Notes

Reaction equation

HRID 1903123 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].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.C(N(C(C)C)C(C)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]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 81001,5-Dibromopentane2×HCID 81531DiisopropylethylamineHCID 603089Ethyl 6-amino-9H-beta-carboline-3-carboxylate

Product 1

HCID 13136254HCID 13136254, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

446 mg of 6-amino-beta-carboline-3-carboxylic-acid-ethylester in 17.5 ml of absolute ethanol is heated together with 410 mg of 1.5-dibromopentane and 500 mg of ethyldiisopropylamine under nitrogen for 4 h at the reflux. After adding 74 mg more of 1,5-dibromopentane, boiling proceeds for another 2 h at the reflux. After evaporation, the remainder is introduced in methylene chloride, washed with saturated bicarbonate solution as well as with saturated NaCl solution, filtered and concentrated. After recrystallizing in alcohol, ethyl acetate and a little ether, 255 mg of 6-(1-piperidinyl)-beta-carboline-3-carboxylic-acid-ethylester, m.p. 255°-256° C., is obtained.

Workup

  1. customfor another 2 h
  2. customAfter evaporation
  3. additionthe remainder is introduced in methylene chloride
  4. washwashed with saturated bicarbonate solution as well as with saturated NaCl solution
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAfter recrystallizing in alcohol

Sources & evidence

ORD record
ord-0e09051adb9e4585bec032625dac2d69
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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