Tetrahydrofuran → N-(2-Azepanylmethyl)-N-ethylethanamine

HRID 465052Notes

Reaction equation

HRID 465052 reaction equation
Cl.[NH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O1[CH2:22][CH2:21]CC1>>[CH2:3]([N:2]([CH2:8][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:2]1)[CH2:21][CH3:22])[CH3:4]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 202171592H-Azepin-2-one, hexahydro-, hydrochloride (1:1)HCID 21226445Aluminium lithium hydride2×

Product 1

HCID 4715268N-(2-Azepanylmethyl)-N-ethylethanamine

Procedure

With external cooling, 7-[(diethylamino)methyl[-hexahydro-2H-azepin-2-one hydrochloride (10.0 g, 0.043 mol) is added in batches to a suspension of lithium aluminium hydride (1.9 g, 0.05 mol) in anhydrous tetrahydrofuran (500 ml) and the mixture is refluxed for 1 hour after the initially violent reaction has ended. The excess lithium aluminium hydride is decomposed by the dropwise addition of 20% sodium hydroxide solution. The tetrahydrofuran phase is separated off from the precipitate formed and concentrated in vacuo. The oily residue remaining is then distilled over caustic potash under water jet vacuum. A colorless oil (4.7 g) is obtained, boiling point 12 mm Hg 102°-105° C.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. customafter the initially violent reaction
  3. customThe tetrahydrofuran phase is separated off from the precipitate
  4. customformed
  5. concentrationconcentrated in vacuo
  6. distillationThe oily residue remaining is then distilled over caustic potash under water jet vacuum

Sources & evidence

ORD record
ord-321072b7d9d9443badb6bafe7f1ccc54
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

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