1,5-Dibromopentane → HCID 19696217, compound

HRID 863532Notes

Reaction equation

HRID 863532 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([Br:16])=[C:8]([NH2:15])[C:9]=2[N+:12]([O-:14])=[O:13])[CH2:4]1.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br.C(N(C(C)C)CC)(C)C.CCOC(C)=O>CN(C=O)C.CO>[NH2:15][C:8]1[C:9]([N+:12]([O-:14])=[O:13])=[C:10]2[C:5](=[CH:6][C:7]=1[Br:16])[CH2:4][CH:3]([N:2]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:11]2

Participants

7

Reactant 4

HCID 81001,5-DibromopentaneHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 19696169HCID 19696169, compound

Product 1

HCID 19696217HCID 19696217, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2,5-diamino-6-bromo-4-nitroindane hydrochloride (1.5 g, 5 mmol), 1,5-dibromopentane (1.4 g, 6 mmol) and diisopropylethylamine (1.3 g, 10 mmol) in DMF (100 mL) was heated at 50° C. for 24 h. The solvent was evaporated and the residue taken up in methylene chloride:water. The aqueous layer was basified with 2N NaOH and back extracted. The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a syrup. The purified product (0.8 g) was obtained from column chromatography (4:1 EtOAc:methanol).

Workup

  1. customThe solvent was evaporated
  2. extractionback extracted
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a syrup

Sources & evidence

ORD record
ord-8cee1852ad344bf0ac5c02ee47043313
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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