3-Hydroxypyridine → Benzyl [2-oxo-2-(piperidin-1-yl)ethyl]carbamate

HRID 441894Notes

Reaction equation

HRID 441894 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na].OC1C=NC=CC=1.C1([O:21][C:22](=O)[CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])C=CC=CC=1>C(OCC)(=O)C>[CH2:28]([O:27][C:25]([NH:24][CH2:23][C:22]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:21])=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 79713-HydroxypyridineHCID 8082PiperidineHCID 357740HCID 357740, compoundHCID 5360545Sodium

Product 1

HCID 21415582Benzyl [2-oxo-2-(piperidin-1-yl)ethyl]carbamateYield 68%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

8.5 g. of piperidine and 1.2 g. of the sodium salt of 3-hydroxypyridine are added to 100 ml. of ethyl acetate, and 28.5 g. benzyloxycarbonylglycine phenyl ester is added thereto with stirring at room temperature, whereupon reaction immediately starts and is complete in 2 hours. The product is worked up as previously described to give an oil which is crystallized from acetone-water. 18.7 g. of N-(benzyloxycarbonylglycyl)piperidine are obtained (yield: 68 percent) m.p. 111° - 112° C. A single spot is obtained therefrom by thin layer chromatography. An additional 5.9 g. of crystals are obtained from the mother liquor, (yield: 21 percent) m.p. 109.5° - 112° C.

Workup

  1. customto give an oil which
  2. customis crystallized from acetone-water

Sources & evidence

ORD record
ord-fecf74de981645d9a30dadf33c679312
Source dataset
uspto-grants-1977_08
Patent number
USRE029369

Reaction notes

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