Water → Ethyl 4-(4-hydroxypiperidin-1-yl)benzoate

HRID 591604Notes

Reaction equation

HRID 591604 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]1.O>CS(C)=O>[OH:19][CH:16]1[CH2:17][CH2:18][N:13]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 79341Piperidin-4-ol

Product 1

HCID 12717445Ethyl 4-(4-hydroxypiperidin-1-yl)benzoateYield 82%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of ethyl 4-fluorobenzoate (16.5 g, 98.1 mmol) and piperidin-4-ol (10.0 g, 98.8 mmol) in DMSO (20 mL) was heated at 120° C. under nitrogen for 48 hours. The mixture was cooled to room temperature, poured into water (400 mL), and the solids were filtered off, washed with water, followed by hexane, to afford ethyl 4-(4-hydroxypiperidin-1-yl)benzoate (20.0 g, 82%).

Workup

  1. filtrationthe solids were filtered off
  2. washwashed with water

Sources & evidence

ORD record
ord-c94a46937c7142a395509c741ae7eb86
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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