Hydrochloric Acid → 1-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinoxalinone dihydrochloride

HRID 656943Notes

Reaction equation

HRID 656943 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.[ClH:29]>CO.C(Cl)Cl.O1CCOCC1>[ClH:29].[ClH:29].[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

6

Reactant 2

HCID 313Hydrochloric AcidHCID 59397942tert-butyl{1-[2-(7-fluoro-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Product 1

HCID 688175421-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-2(1H)-quinoxalinone dihydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl {1-[2-(7-fluoro-2-oxo-1(2H)-quinoxalinyl)ethyl]-4-piperidinyl}carbamate (4.0 g) in dry MeOH (15 ml) and dry DCM (30 ml) was treated with 4 M hydrogen chloride in 1,4-dioxane (30 ml) and stirred at rt for 3 h. It was evaporated to dryness and the insoluble product was heated in MeOH (50 ml), cooled, filtered, washed with cold MeOH, then ether, to give a solid (3.05 g).

Workup

  1. customIt was evaporated to dryness
  2. temperaturethe insoluble product was heated in MeOH (50 ml)
  3. temperaturecooled
  4. filtrationfiltered
  5. washwashed with cold MeOH

Sources & evidence

ORD record
ord-bc5bdbbbba6f47a1814e09d0deb45f80
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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