2-Phenylpropionic acid → 1-(4-Hydroxypiperidin-1-yl)-3-phenylpropan-1-one

HRID 584720Notes

Reaction equation

HRID 584720 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]1([CH2:14][CH2:15][C:16](Cl)=[O:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(C(C)C(O)=O)C=CC=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:8]1([CH2:14][CH2:15][C:16]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[O:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 102962-Phenylpropionic acidHCID 14798Sodium HydroxideHCID 64801Benzenepropanoyl chlorideHCID 79341Piperidin-4-ol

Product 1

HCID 221751621-(4-Hydroxypiperidin-1-yl)-3-phenylpropan-1-oneYield 39%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

This amine was synthesized in accordance with the method of Scheme 37. To 4 g (40 mmol) of 4-hydroxypiperidine in 20 mL of toluene was added phenylpropionyl chloride (derived from 6 g (40 mmol) of phenylpropionic acid in excess thionyl chloride). To the mixture was added excess 2N aqueous NaOH. After stirring 24 hours, the toluene layer was discarded and the aqueous phase was extracted with CH2Cl2, dried, and evaporated under vacuum to give 3.63 g (39%) of 1-(3-phenylpropionyl)-4-hydroxypiperidine (134). GC/MS indicated 100% purity with a molecular ion of 233.

Workup

  1. extractionthe aqueous phase was extracted with CH2Cl2
  2. customdried
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-4aaa411c929e403e9ecc69ab41cbaa19
Source dataset
uspto-grants-2005_08
Patent number
US06927225B2

Reaction notes

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