Hydrochloric Acid → (1,4-diazepan-1-yl)(furan-2-yl)methanone

HRID 838971Notes

Reaction equation

HRID 838971 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](Cl)=[O:15].[OH-].[Na+]>O>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([N:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 68163Hexahydro-1,4-diazepineHCID 682422-Furancarbonyl chloride

Product 1

HCID 12694336(1,4-diazepan-1-yl)(furan-2-yl)methanoneYield 53.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Homopiperazine (70 g) in 160 ml H2O was treated with hydrochloric acid (1 part conc. HCl and 1 part water) until the pH of the solution was 5.5. Furoyl chloride (79.5 g) and 25% NaOH was added simultaneously to maintain a pH between 4.5 and 5.5. Then 50% sodium hydroxide was added until the pH reached 9.5. The solution was extracted with chloroform, dried over potassium carbonate and distilled giving 63.24 g of product. bp 125°-130° C, 10.2mm.

Workup

  1. temperatureto maintain a pH between 4.5 and 5.5
  2. extractionThe solution was extracted with chloroform
  3. dry with materialdried over potassium carbonate
  4. distillationdistilled

Sources & evidence

ORD record
ord-4929b3f60c5348739be35c8ba7f593ac
Source dataset
uspto-grants-1978_06
Patent number
US04093726

Reaction notes

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