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

HRID 656989Notes

Reaction equation

HRID 656989 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.ClCCl.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 dihydrochlorideYield 99%

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 (8.72 g, 22.36 mmol) in methanol (90 ml) and dichloromethane (150 mL) was treated with 4 M hydrogen chloride in 1,4-dioxane (150 mL) (added in a slow stream, some exotherm and rapid precipitation observed) and stirred at room temperature for 2.5 h. The mixture was evaporated to dryness and the residue was triturated with ether. The solid was filtered off, washed with ether and dried to give the amine salt as a grey-green solid (8.06 g, 99%).

Workup

  1. additionadded in a slow stream
  2. customsome exotherm and rapid precipitation
  3. customThe mixture was evaporated to dryness
  4. customthe residue was triturated with ether
  5. filtrationThe solid was filtered off
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-c68060719ec646f6a90dbe073ba3f5a6
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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