Pyridine → N-(6-Acetoxyhexyl)-N-methylaniline

HRID 1199285Notes

Reaction equation

HRID 1199285 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].N1C=CC=CC=1>>[C:16]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([CH3:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 152539786-[Methyl(phenyl)amino]hexan-1-OL

Product 1

HCID 19697246N-(6-Acetoxyhexyl)-N-methylaniline

Procedure

A mixture of 210 g (1.01 mol) of N-(6-hydroxyhexyl)-N-methylaniline (Example 1), 112 g (1.10 mol) of acetic anhydride, and 86 g (1.1 mol) of pyridine was heated at reflux with stirring for 2 hours. After cooling, the solution was poured onto 500 g of ice and extracted with ethyl acetate (4×300 mL). The combined extracts were dried (MgSO4) and the solvent was removed at reduced pressure. The residue was distilled in vacuo, collecting the fraction boiling at 130° C. (0.01 mm). Yield: 231 g (93%) of a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate (4×300 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent was removed at reduced pressure
  7. distillationThe residue was distilled in vacuo
  8. customcollecting the fraction boiling at 130° C. (0.01 mm)

Sources & evidence

ORD record
ord-67d392e9c24e42d3ad89e31a638dc9a4
Source dataset
uspto-grants-1990_02
Patent number
US04900127

Reaction notes

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