Acetic Anhydride → HCID 86698039, compound

HRID 518889Notes

Reaction equation

HRID 518889 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:21]=[CH:20][C:18]([NH2:19])=[C:17]([O:22][CH:23]([CH3:25])[CH3:24])[CH:16]=2)[CH2:11][CH2:10]1>C(O)=O>[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:21]=[CH:20][C:18]([NH:19][CH:1]=[O:3])=[C:17]([O:22][CH:23]([CH3:25])[CH3:24])[CH:16]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 683600014-(1-Methylpiperidin-4-yl)-2-(propan-2-yloxy)aniline

Product 1

HCID 86698039HCID 86698039, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

A solution of 12.3 g of acetic anhydride is added slowly to 19 ml of formic acid at ambient temperature. After one hour of stirring, a solution of 6.0 g of 4-(1-methylpiperidin-4-yl)-2-(propan-2-yloxy)aniline in 28 ml of formic acid is added dropwise. The mixture is stirred at ambient temperature for 2 h and then concentrated under vacuum and taken up with water. The aqueous phase is neutralized with a saturated sodium bicarbonate solution and extracted three times with 100 ml of dichoromethane. The organic phases are dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product is triturated with ethyl ether and the solid is filtered off, so as to obtain 5.0 g of N-[4-(1-methylpiperidin-4-yl)-2-(propan-2-yloxy)phenyl]formamide.

Workup

  1. stirringThe mixture is stirred at ambient temperature for 2 h
  2. concentrationconcentrated under vacuum
  3. extractionextracted three times with 100 ml of dichoromethane
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude product is triturated with ethyl ether
  8. filtrationthe solid is filtered off

Sources & evidence

ORD record
ord-5b8065186a884698bc84024d20283e35
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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