Hydrochloric Acid → 8,9,10,11-Tetrahydropyrazino[1',2':1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride

HRID 1364032Notes

Reaction equation

HRID 1364032 reaction equation
[ClH:1].[NH2:2][C:3]1[C:12]2[N:13]=[C:14]3[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16][N:15]3[C:11]=2[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1>O1CCOCC1.ClCCl>[ClH:1].[CH:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[C:11]1[N:15]3[CH2:16][CH2:17][NH:18][CH2:19][C:14]3=[N:13][C:12]=1[C:3]([NH2:2])=[N:4]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58923896tert-butyl 6-amino-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

Product 1

HCID 669586758,9,10,11-Tetrahydropyrazino[1',2':1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride (300 mL of a 4 N solution in 1,4-dioxane) was added to a solution of tert-butyl 6-amino-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate (34.74 g, 102.36 mmol) in dichloromethane (300 mL). The reaction was stirred overnight at ambient temperature and then concentrated under reduced pressure. The resulting solid was suspended in dichloromethane, isolated by filtration, and washed sequentially with dichloromethane, diethyl ether, hexane, and diethyl ether. The solid was then triturated with methanol and isolated by filtration to provide 11.58 g of 8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride as a white solid. The filtrate was concentrated under reduced pressure, dissolved in water, and precipitated with 1,4-dioxane to provide an additional 6.95 g of product.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customisolated by filtration
  3. washwashed sequentially with dichloromethane, diethyl ether, hexane, and diethyl ether
  4. customThe solid was then triturated with methanol
  5. customisolated by filtration

Sources & evidence

ORD record
ord-576ce7cd1a7a4faaa226395ec87ddb73
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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