Ethyl formate → Hexahydro-1H-azepine-1-carbaldehyde

HRID 846859Notes

Reaction equation

HRID 846859 reaction equation
[CH:1](OCC)=[O:2].[NH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>>[CH:1]([N:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:2]

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 8119Azepane

Product 1

HCID 91280Hexahydro-1H-azepine-1-carbaldehydeYield 84%

Procedure

Ethyl formate (22.2 G, 0.3M) was added dropwise under nitrogen to hexahydro-1H-azepine (19.8 G, 0.2M) in such a way that a gentle reflux is maintained during the addition. The reaction mixture was then allowed to stir overnight. The volatile materials were evaporated at room temperature and ~20 mm. The residue was distilled in vacuo to give 1-(Formyl)-Hexahydro-1H-Azepine (bp. 56°-8°/3-4 mm; 84%).

Workup

  1. temperaturea gentle reflux
  2. temperatureis maintained during the addition
  3. customThe volatile materials were evaporated at room temperature
  4. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-fce3fa6da45c4c75ae0d32641980e161
Source dataset
uspto-grants-1992_08
Patent number
US05138050

Reaction notes

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