Acetic Anhydride → 1-Formylpiperidine-4-carbonyl chloride

HRID 370878Notes

Reaction equation

HRID 370878 reaction equation
S(Cl)([Cl:3])=O.[CH:5]([N:7]1[CH2:15][CH2:14][CH:10]([C:11](O)=[O:12])[CH2:9][CH2:8]1)=[O:6].C(OC(=O)C)(=O)C>>[CH:5]([N:7]1[CH2:15][CH2:14][CH:10]([C:11]([Cl:3])=[O:12])[CH2:9][CH2:8]1)=[O:6]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 24386Thionyl ChlorideHCID 27592321-Formyl-4-piperidinecarboxylic Acid

Product 1

HCID 132242561-Formylpiperidine-4-carbonyl chlorideYield 100%

Procedure

To 100 ml of freshly distilled thionyl chloride was added 30 g of N-formylisonipecotic acid at 0°. After the addition was complete, 2 ml of acetic anhydride was added and the solution was stirred at 20° for three hrs. The reaction mixture was diluted with 3 400-ml portions of petroleum ether, bp, 60°-80°. The resulting solid was collected, washed with 50 ml of ether and dried under vacuum over phosphorous pentoxide to yield 33.5 g (100%) of N-formylisonipecotic acid chloride.

Workup

  1. additionAfter the addition
  2. customThe resulting solid was collected
  3. washwashed with 50 ml of ether
  4. dry with materialdried under vacuum over phosphorous pentoxide

Sources & evidence

ORD record
ord-9eb68f4afc344735b15231e35548365b
Source dataset
uspto-grants-1985_07
Patent number
US04528376

Reaction notes

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