Dimethylformamide → Butyl 4-oxopiperidine-1-carboxylate

HRID 2229189Notes

Reaction equation

HRID 2229189 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.C(N([CH2:15][CH3:16])CC)C.[C:17]([O:20][C:21]([O-])=O)([O-])=[O:18].[CH3:24]N(C)C=O>>[CH2:21]([O:20][C:17]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)=[O:18])[CH2:24][CH2:15][CH3:16]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 2723901PiperonylamineHCID 15238643Pyrocarbonate

Product 1

HCID 22732029Butyl 4-oxopiperidine-1-carboxylate

Procedure

About 2 g of 4-piperidone hydrochloride monohydrate (FIG. 10a) was dissolved in about 30 ml of N,N-dimethylformamide at temperatures of between about 110-115° C. The solution was cooled to room temperature, and to this solution was added about 2.6 g of triethyl amine and a solution containing about 3.06 g of ditertarybutyl dicarbonate in 10 ml DMF. The reaction was continued for about 24 hours at room temperature. The DMF was removed under reduced pressure. About 100 ml of water was added to the residue and the mixture was extracted with ethyl ether (2×100 ml), and the organic layer dried over anhydrous MgSO4. The ether was evaporated to dryness under reduced pressure to yield about 2.33 g of the compound of FIG. 10b.

Workup

  1. customThe DMF was removed under reduced pressure
  2. additionAbout 100 ml of water was added to the residue
  3. extractionthe mixture was extracted with ethyl ether (2×100 ml)
  4. dry with materialthe organic layer dried over anhydrous MgSO4
  5. customThe ether was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f73a84b269f4451bb2a370f803eab873
Source dataset
uspto-grants-2002_07
Patent number
US06420370B1

Reaction notes

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