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

HRID 1982907Notes

Reaction equation

HRID 1982907 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+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>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

8

Reactant 4

HCID 68163Hexahydro-1,4-diazepineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 178419358HCID 178419358, compound

Product 1

HCID 178420600HCID 178420600, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent

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

Sources & evidence

ORD record
ord-d1287e59f77245d497f1af5792a1b932
Source dataset
uspto-grants-2009_06
Patent number
US07541370B2

Reaction notes

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