Acetic Anhydride → Acetamide, N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-

HRID 847736Notes

Reaction equation

HRID 847736 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:19](=[O:21])[CH3:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 9971484Acetamide, N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

One gram of 3-[3-(1-piperidinylmethyl)phenoxy]propylamine was dissolved in 1 ml of pyridine, and 0.5 ml of acetic anhydride was added. The mixture was allowed to stand at room temperature for 4 hours. The solvent was distilled off under reduced pressure, and small amounts of water and potassium carbonate were added. The mixture was extracted with chloroform, washed with water, and dried. Then, the solvent was distilled off. The residue was purified by TLC (developing solvent: chloroform/methanol=9/l) to afford 753 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl] acetamide as an oil.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and small amounts of water and potassium carbonate
  2. additionwere added
  3. extractionThe mixture was extracted with chloroform
  4. washwashed with water
  5. customdried
  6. distillationThen, the solvent was distilled off
  7. customThe residue was purified by TLC (developing solvent: chloroform/methanol=9/l)

Sources & evidence

ORD record
ord-670439af131b4b1bad07579f24e2c5ff
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

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