Trifluoroacetic acid → 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one

HRID 255306Notes

Reaction equation

HRID 255306 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:28])[N:9]2[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][CH2:15]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:20][CH:17]1[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][N:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=3)[N:6]=[CH:7][C:8]2=[O:28])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59397942tert-butyl{1-[2-(7-fluoro-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate2×

Product 1

HCID 593979071-(2-(4-aminopiperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl {1-[2-(7-fluoro-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 141, 240 mg, 0.62 mmol) in dichloromethane (20 mL) was treated with trifluoroacetic acid (15 mL). After 45 minutes, the reaction was concentrated to dryness, the residue taken up in methanol/chloroform (15:85, 30 mL) and washed with saturated sodium bicarbonate solution. The aqueous layer was re-extracted with methanol/chloroform (15:85, 3×30 mL. The combined organic phases were dried over magnesium sulfate and concentrated to dryness to give 170 mg (quantitative) of the crude product as an oil.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. washwashed with saturated sodium bicarbonate solution
  3. extractionThe aqueous layer was re-extracted with methanol/chloroform (15:85, 3×30 mL
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-05f76c2fa60947c28f0a9dc175c3a751
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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