Acetonitrile → 4-Azepan-1-ylbenzaldehyde

HRID 1944535Notes

Reaction equation

HRID 1944535 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10](#[N:12])[CH3:11]>>[N:12]1([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:4][CH2:3][CH2:2][CH2:9][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 680234-Fluorobenzaldehyde

Product 1

HCID 25078674-Azepan-1-ylbenzaldehyde

Procedure

A solution of 4-fluoro-benzaldehyde (2.59 mL, 24.2 mmol) and hexamethyleneimine (8.2 mL, 72 mmol) in acetonitrile (40 mL) was heated at reflux for 16 hours. The product was preabsorbed onto silica gel and purified by flash silica gel chromatography, using ethyl acetate (10-15%) in hexane as the eluant, to give the product, 5.0 g (100%). MS: m/z 204 (MH+). 1H NMR (CDCl3): 1.53-1.59 (m, 4 H), 1.78-1.82 (m, 4 H), 3.53 (t, 4 H), 6.70 (d, 2 H), 7.70 (d, 2 H) and 9.70 (s, 1 H).

Workup

  1. temperatureat reflux for 16 hours
  2. customThe product was preabsorbed onto silica gel
  3. custompurified by flash silica gel chromatography
  4. customto give the product, 5.0 g (100%)

Sources & evidence

ORD record
ord-8498722b2cdd4d9695745249806e8617
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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