Tyrosol → HCID 22633982, compound

HRID 1250928Notes

Reaction equation

HRID 1250928 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.Cl[CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:14]1([CH2:13][CH2:12][O:1][C:2]2[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 10393TyrosolHCID 11430Potassium CarbonateHCID 748271-(2-Chloroethyl)piperidine

Product 1

HCID 22633982HCID 22633982, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-hydroxyphenethyl alcohol (5.02 g, 36.3 mmol) and chloroethyl piperidine (7.36 g, 39.96 mmol) in 30 ml of DMF, 5 g of K2CO3 was added. The reaction was stirred at 80° C. overnight. After cooling the mixture was quenched with water then extracted in CHCl3. The organic layer was separated, dried over Na2SO4, filtered and concentrated. 2-[4-(2-Piperidin-1-yl-ethoxy)-phenyl]-ethanol (4.58 g, 18.4 mmol) was isolated as a brown oil; Yield 51%; MS: 250.3 (M+H)+

Workup

  1. temperatureAfter cooling the mixture
  2. customwas quenched with water
  3. extractionthen extracted in CHCl3
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-10517de05eec40e58d9a4a016b87e5e9
Source dataset
uspto-grants-2002_01
Patent number
US06340691B1

Reaction notes

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