Azepane → 3-Azepan-1-ylpropan-1-ol

HRID 1979906Notes

Reaction equation

HRID 1979906 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:9][CH2:10][CH2:11][OH:12].[OH-].[K+]>C(O)C>[OH:12][CH2:11][CH2:10][CH2:9][N:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8119AzepaneHCID 123133-Chloro-1-propanolHCID 14797Potassium Hydroxide

Product 1

HCID 105588853-Azepan-1-ylpropan-1-olYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1 mole of azepane and 0.5 mole of 3-chloro-1-propanol in 500 ml of ethanol was refluxed for 18 hours. The reaction mixture was treated with 0.55 mole of KOH and refluxed for 0.75 hour. Cooling, filtration and distillation yielded 88% of N-(3-hydroxypropyl)azepane (b.p.=136° C. at 21 mm; analysis for C9H19NO, calculated: %N=8.91; found: %N=8.30).

Workup

  1. temperaturerefluxed for 0.75 hour
  2. temperatureCooling
  3. filtrationfiltration and distillation

Sources & evidence

ORD record
ord-8f3aa081a5ea49de891125a45b7c7581
Source dataset
uspto-grants-1984_11
Patent number
US04483833

Reaction notes

Loading…