(2-(2-Morpholinoethylamino)-3-fluorophenyl)methanol → 2-(2-Morpholinoethylamino)-3-fluorobenzaldehyde

HRID 1695942Notes

Reaction equation

HRID 1695942 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([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])[CH2:3][CH2:2]1>C1(C)C=CC=CC=1.O=[Mn]=O>[O:1]1[CH2:2][CH2:3][N:4]([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])[CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 57774478(2-(2-Morpholinoethylamino)-3-fluorophenyl)methanol

Product 1

HCID 577744152-(2-Morpholinoethylamino)-3-fluorobenzaldehydeYield 71.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

(2-(2-Morpholinoethylamino)-3-fluorophenyl)methanol (695 mg, 2.733 mmol) was stirred with MnO2 (966 mg, 11.11 mmol) in toluene (12 mL) at 115° C. for 2 days. The reaction was filtered through a plug of Celite with CH2Cl2 and the crude product was purified by ISCO chromatography eluting with EtOAc/Hex (12 g redisep column, 5-40% gradient over 30 CV) to give 2-(2-morpholinoethylamino)-3-fluorobenzaldehyde (495 mg). FIA: 253.17 (M+1)

Workup

  1. filtrationThe reaction was filtered through a plug of Celite with CH2Cl2
  2. customthe crude product was purified by ISCO chromatography
  3. washeluting with EtOAc/Hex (12 g redisep column, 5-40% gradient over 30 CV)

Sources & evidence

ORD record
ord-f01f0259b89b400580b0c56451809c13
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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