Acetic Anhydride → HCID 57617609, compound

HRID 1518061Notes

Reaction equation

HRID 1518061 reaction equation
CCN(C(C)C)C(C)C.[O:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH2:17])[CH2:12][CH2:11]1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>C(Cl)Cl>[O:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 27732104-Aminomethyltetrahydropyran

Product 1

HCID 57617609HCID 57617609, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PS-DIEA (Argonaut Technologies, 1.35 g, 4.5 mmol) is added to a mixture of C-(tetrahydropyran-4-yl)methylamine (345 mg, 3.0 mmol) in CH2Cl2 (20 ml) at ambient temperature. Acetic anhydride (367 mg, 3.6 mmol) is added to the mixture. After stirring at ambient temperature for 18 hours, methylisocyanate polystyrene (Novabiochem, 1.84 g, 3.0 mmol) and N-(2-aminoethyl)aminomethyl polystyrene (Novabiochem, 1.07 g, 3.0 mmol) are added. After stirring at room temperature for 4 h, the resins are removed by filtration, and the resins are washed with dichloromethane. The filtrate and washing are combined, and the solvent is removed by evaporation in vacuo to give N-(tetrahydropyran-4-ylmethyl)acetamide.

Workup

  1. stirringAfter stirring at room temperature for 4 h
  2. customthe resins are removed by filtration
  3. washthe resins are washed with dichloromethane
  4. washThe filtrate and washing
  5. customthe solvent is removed by evaporation in vacuo

Sources & evidence

ORD record
ord-d11cf24eb98d412d94f1968547b7d5db
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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