4-Piperidineethanol → HCID 67206122, compound

HRID 1023838Notes

Reaction equation

HRID 1023838 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.C([O-])(O)=O.[Na+].[CH3:15][C:16]([CH3:22])([CH3:21])[CH2:17][C:18](Cl)=[O:19]>ClCCl>[OH:9][CH2:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([C:18](=[O:19])[CH2:17][C:16]([CH3:22])([CH3:21])[CH3:15])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 739534-PiperidineethanolHCID 815143,3-Dimethylbutanoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 67206122HCID 67206122, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(piperidin-4-yl)ethanol (0.30 g, 2.32 mmol) in anhydrous dichloromethane (10 mL), NaHCO3 (0.59 g, 6.97 mmol) was added. The suspension was cooled to 0° C. and then 3,3-dimethylbutanoyl chloride (0.38 g, 2.79 mmol) was added dropwise over a period of 15 min. The reaction was followed by TLC till the disappearance of the starting material (overnight) and was then filtered. The residue was then purified using column chromatography on a silica gel column eluting with a solution of ethyl acetate in hexane (50%) to produce the alcohol in a 45% yield.

Workup

  1. customwas followed by TLC till the disappearance of the starting material (overnight)
  2. filtrationwas then filtered
  3. customThe residue was then purified
  4. washeluting with a solution of ethyl acetate in hexane (50%)

Sources & evidence

ORD record
ord-daa69363e0594b118ec804e3dc912eef
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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