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

HRID 1577320Notes

Reaction equation

HRID 1577320 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)methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Homopiperazine (70 g., 0.70 mole) in 160 ml. water was treated with 6 N hydrochloric acid to adjust to pH 5.5 Furoyl chloride (79.5 g., 0.60 mole) and 25% (w/w) aqueous sodium hydroxide solution were added simultaneously to maintain a pH of 4.5-5.5. Then additional sodium hydroxide was added to bring the mixture to pH 9.5. The solution was extracted with chloroform, dried over anhydrous potassium carbonate and distilled to afford 63 g. of product, B.P. 124°-130° C. at 10 mm.

Workup

  1. additionwere added simultaneously
  2. temperatureto maintain a pH of 4.5-5.5
  3. extractionThe solution was extracted with chloroform
  4. dry with materialdried over anhydrous potassium carbonate
  5. distillationdistilled
  6. customto afford 63 g

Sources & evidence

ORD record
ord-16170bd14ddd4d5ea4f0084fbdfb18e2
Source dataset
uspto-grants-1981_09
Patent number
US04287341

Reaction notes

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