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

HRID 1092168Notes

Reaction equation

HRID 1092168 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:14](=O)[CH3:15])[CH2:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Cl>C1COCC1>[CH2:14]([N:7]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4186202N-AcetylhomopiperazineHCID 21226445Aluminium lithium hydride

Product 1

HCID 75775381-Ethyl-1,4-diazepaneYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (38.2 ml, 38.19 mmol) was added to 1-(1,4-diazepan-1-yl)ethanone (1.697 g, 11.93 mmol) in THF (59.7 ml) at 0° C. under nitrogen. The resulting solution was stirred at ambient temperature for 1 h and then at 60° C. for 1 h. The cooled reaction mixture was poured onto ice (500 mL), acidified with HCl (2M aqueous solution) and purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford 1-ethyl-1,4-diazepane (0.610 g, 40%) as a yellow liquid. This was used directly with no further purification.

Workup

  1. waitat 60° C. for 1 h
  2. customThe cooled reaction mixture
  3. additionwas poured onto ice (500 mL)
  4. custompurified by ion exchange chromatography
  5. washThe desired product was eluted from the column
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-ecdc050cda294b7d9497d2d4d20dfb3e
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

Loading…