Diketene → HCID 43579637, compound

HRID 1055221Notes

Reaction equation

HRID 1055221 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[CH2:8]=[C:9]1[O:13][C:11](=[O:12])[CH2:10]1>O1CCCC1>[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:11](=[O:12])[CH2:10][C:9](=[O:13])[CH3:8])[CH2:3]1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 232933-Hydroxypiperidine

Product 1

HCID 43579637HCID 43579637, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 36.10 g (0.36 mol) of 3-hydroxypiperidine in 300 ml tetrahydrofuran was added dropwise to a solution of 30 g of diketene (0.36 mol) in 200 ml tetrahydrofuran at −5 to 0° C. After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography. The reaction mixture was evaporated and the residue purified by column chromatography. This gave 53.53 g (0.29 mol, 81% yield) of a white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-ec9d864d77b546acbc81e183a04b4fcc
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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