Hexahydro-1,4-diazepine → HCID 178420600, compound

HRID 225428Notes

Reaction equation

HRID 225428 reaction equation
Br[C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH:11]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.CC([O-])(C)C.[Na+]>CC1C=CC=CC=1C.O.[Pd]>[N:11]1([C:2]2[C:10]3[NH:9][CH:8]=[N:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

7

Reactant 3

HCID 68163Hexahydro-1,4-diazepineHCID 23676156Sodium t-butoxideHCID 178419358HCID 178419358, compound

Product 1

HCID 178420600HCID 178420600, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 4-bromobenzimidazole (42 mmol), homopiperazine (256 mmol) and NaOt-Bu (59 mmol) in dry o-xylene, under N2, is treated with a catalytic amount of Pd (OCOCH3)2·P(t-Bu)3 (P/Pd=4), heated at 120° C. for 3 hr, cooled to room temperature and diluted with water. The aqueous mixture is extracted with ethyl acetate. The extracts are combined, dried over MgSO4 and concentrated in vacuo to give a residue. The residue is purified by flash chromatography to give 4-(homopiperazin-1-yl)benzimidazole.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe aqueous mixture is extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-acb0fdec938349bfba9edaea14747266
Source dataset
uspto-grants-2009_07
Patent number
US07557098B2

Reaction notes

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