Potassium Carbonate → 4-(4-Hydroxypiperidin-1-yl)benzaldehyde

HRID 2072610Notes

Reaction equation

HRID 2072610 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.F[C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 79341Piperidin-4-ol

Product 1

HCID 127174464-(4-Hydroxypiperidin-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

A 2 liter three necked flask fitted with a mechanical stirrer, thermometer and condenser is charged with 180 g of 4-hydroxypiperidine, 74.4 g of 4-fluorobenzaldehyde, 1 ml of Aliquot 336, 750 ml of dimethylsulfoxide and 82.8 g of anhydrous potassium carbonate. The mixture is heated at 95° C. for three days, then the product mixture is cooled and poured into 3 liters of ice water. The resultant solid precipitate is filtered, washed with water, and vacuum dried. The crude product is recrystallized from toluene, m.p. 115°-118° C.

Workup

  1. temperaturethe product mixture is cooled
  2. filtrationThe resultant solid precipitate is filtered
  3. washwashed with water, and vacuum
  4. customdried
  5. customThe crude product is recrystallized from toluene, m.p. 115°-118° C.

Sources & evidence

ORD record
ord-2cea1c96852a4c4eba3a53f38de704a0
Source dataset
uspto-grants-1990_04
Patent number
US04913845

Reaction notes

Loading…