Acetic-formic anhydride → HCID 21080301, compound

HRID 346667Notes

Reaction equation

HRID 346667 reaction equation
[CH:1](OC(=O)C)=[O:2].[N:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([O:19][C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1>>[N:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([O:19][C:20]3[CH:26]=[CH:25][C:23]([NH:24][CH:1]=[O:2])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 18357062HCID 18357062, compound

Product 1

HCID 21080301HCID 21080301, compoundYield 65.2%

Procedure

Acetic formic anhydride (1.5 g; pre-formed by heating acetic anhydride and 98% formic acid at 60° C. for 2 hours) was cooled to 5° C. and 4-[1-(4-pyridyl)piperidin-4-yloxy]aniline (1.0 g) was added. The mixture was stirred at ambient temperature for 16 hours and then evaporated. The residue was dissolved in water (50 ml) and the mixture was basified to pH10 by the addition of a 2M aqueous sodium hydroxide solution. The resultant mixture was extracted with methylene chloride, washed with water and with brine, dried (MgSO4) and evaporated to give N-{4-[1-(4-pyridyl)piperidin-4-yloxy]phenyl}formamide as a foam (0.72 g);

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in water (50 ml)
  3. additionthe mixture was basified to pH10 by the addition of a 2M aqueous sodium hydroxide solution
  4. extractionThe resultant mixture was extracted with methylene chloride
  5. washwashed with water and with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-9d90d39f9635411f8462321bafdde16a
Source dataset
uspto-grants-2007_02
Patent number
US07173025B1

Reaction notes

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