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

HRID 2292211Notes

Reaction equation

HRID 2292211 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+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].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

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 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 Aliquat 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-814ee3e31ee647e593b5c3c63d378846
Source dataset
uspto-grants-1989_01
Patent number
US04801670

Reaction notes

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