Diketene → HCID 60933777, compound

HRID 1055223Notes

Reaction equation

HRID 1055223 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.[CH2:9]=[C:10]1[O:14][C:12](=[O:13])[CH2:11]1>O1CCCC1>[OH:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:12](=[O:13])[CH2:11][C:10](=[O:14])[CH3:9])[CH2:2]1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 60933777HCID 60933777, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 25 g (0.22 mol) of 3-piperidinemethanol in 200 ml tetrahydrofuran was added dropwise to a solution of 18 g of diketene (0.2 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 31.50 g (0.16 mol, 74% yield) of a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-306c9ff897df4881b55f5439b33beee2
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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