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

HRID 442104Notes

Reaction equation

HRID 442104 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

70 g. hexahydro-1,4-diazepine was dissolved in 160 ml. water. Hydrochloric acid (20%) was added until the pH was 5.5. Using a pH meter to keep the pH between 4.5 and 5.5, 79.5 g. furoyl chloride was added in portions along with 25% sodium hydroxide. After addition, 50% sodium hydroxide was added to raise the pH to 9.5. The solution was extracted with chloroform 4 times, the chloroform extracts dried over anhydrous potassium carbonates and the solution distilled giving 53.24 g. product. b.p. 125° - 130°

Workup

  1. additionwas added
  2. temperatureto raise the pH to 9.5
  3. extractionThe solution was extracted with chloroform 4 times
  4. dry with materialthe chloroform extracts dried over anhydrous potassium carbonates
  5. distillationthe solution distilled
  6. customgiving 53.24 g

Sources & evidence

ORD record
ord-0fc6127f064641638645cc30feb5fa5d
Source dataset
uspto-grants-1977_08
Patent number
US04044135

Reaction notes

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