Hydrochloric Acid → Ethyl 1,4-diazepane-1-carboxylate

HRID 704387Notes

Reaction equation

HRID 704387 reaction equation
Cl.[NH:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C([O-])(=O)C.[Na+].Cl[C:15]([O:17][CH2:18][CH3:19])=[O:16]>O>[N:2]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 68163Hexahydro-1,4-diazepineHCID 517045Sodium Acetate

Product 1

HCID 15289249Ethyl 1,4-diazepane-1-carboxylateYield 67.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2N Hydrochloric acid was added to a solution of 1.10 g of homopiperazine in 15 ml of water at room temperature until a pH of 2 was attained. Then, 40% aqueous sodium acetate and 1.28 g of ethyl chloroformate were added alternately in portions within the pH range of 2.0 to 3.5, and the resultant mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with ethyl acetate, and the aqueous layer was saturated with potassium carbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 1.27 g of ethyl 1-homopiperazinecarboxylate.

Workup

  1. washThe reaction mixture was washed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eac1aaa8fd5c421787d2501afd197cb9
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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