Acetic Anhydride → N-{4-[(Oxan-2-yl)oxy]nonyl}acetamide

HRID 1288343Notes

Reaction equation

HRID 1288343 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][NH2:12].[C:18](OC(=O)C)(=[O:20])[CH3:19]>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][NH:12][C:18](=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 203276844-(2-Tetrahydropyranyloxy)nonylamine

Product 1

HCID 21503928N-{4-[(Oxan-2-yl)oxy]nonyl}acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred, ice cold solution of 4-(2-tetrahydropyranyloxy)nonylamine (7.29 g., 0.03 mole) in pyridine (40 ml.) is added acetic anhydride (3.06 g., 0.03 mole) at such a rate as to maintain the reaction temperature at 5°-10°C. The reaction is then allowed to stand at room temperature for 6 hours, poured into ice water (200 ml.) and extracted with ether (2 × 100 ml.). The ether is extracted with ice cold 5% hydrochloric acid (2 × 20 ml.), washed with brine (2 × 25 ml.), then dried over sodium sulfate. Evaporation in vacuo affords the subject compound as a pale yellow oil.

Workup

  1. temperatureto maintain the reaction temperature at 5°-10°C
  2. extractionextracted with ether (2 × 100 ml.)
  3. extractionThe ether is extracted with ice cold 5% hydrochloric acid (2 × 20 ml.)
  4. washwashed with brine (2 × 25 ml.)
  5. dry with materialdried over sodium sulfate
  6. customEvaporation in vacuo

Sources & evidence

ORD record
ord-76b123cd98964ac4b1f91c6f6c15d31a
Source dataset
uspto-grants-1976_10
Patent number
US03987091

Reaction notes

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