Acetyl chloride → (S)-5-aminopiperidin-2-one hydrochloride

HRID 2239749Notes

Reaction equation

HRID 2239749 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][C@@H:5]([NH:8]C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.C([Cl:19])(=O)C.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(O)C>[ClH:19].[NH2:8][C@@H:5]1[CH2:6][NH:7][C:2](=[O:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 15466433(S)-tert-butyl 6-oxopiperidin-3-ylcarbamate

Product 1

HCID 42614518(S)-5-aminopiperidin-2-one hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

N-((3S)-6-Oxo(3-piperidyl))(tert-butoxy)carboxamide (3.9 mmol, 0.83 g) were dissolved in ethanol (10 mL) and cooled to 0° C. Acetyl chloride (2 mL) was added and the reaction was allowed to reach room temperature. The reaction was stirred for 1 hour after which the solvent was removed in vacuo to yield the title compound (725 mg, 99% yield) as the dihydrochloride salt. ES-MS: 115 (M+1).

Workup

  1. customto reach room temperature
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-378afabc157941deb50e0323369a44f3
Source dataset
uspto-grants-2010_05
Patent number
US07723340B2

Reaction notes

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