(2-(2-(Piperidin-1-yl)ethylamino)-3-fluorophenyl)methanol → 2-(2-(Piperidin-1-yl)ethylamino)-3-fluorobenzaldehyde

HRID 1695929Notes

Reaction equation

HRID 1695929 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:17][OH:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1(C)C=CC=CC=1.O=[Mn]=O>[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:17]=[O:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57774402(2-(2-(Piperidin-1-yl)ethylamino)-3-fluorophenyl)methanol

Product 1

HCID 577744132-(2-(Piperidin-1-yl)ethylamino)-3-fluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

(2-(2-(piperidin-1-yl)ethylamino)-3-fluorophenyl)methanol (453 mg, 1.795 mmol) and MnO2 (692 mg, 7.960 mmol) were heated in toluene (15 mL) at reflux overnight. The suspension was filtered through Celite with CH2Cl2 and concentrated on a rotary evaporator. Crude 2-(2-(piperidin-1-yl)ethylamino)-3-fluorobenzaldehyde was carried on to the next reaction.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe suspension was filtered through Celite with CH2Cl2
  3. concentrationconcentrated on a rotary evaporator
  4. customCrude 2-(2-(piperidin-1-yl)ethylamino)-3-fluorobenzaldehyde was carried on to the next reaction

Sources & evidence

ORD record
ord-86435a16b620414f925a41ddab357764
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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