tert-butyl N-(3-(1,2,3,4-tetrahydroquinoxalin-3-on-1-carbonyl)benzyl)-N-methylcarbamate → 3-(Methylaminomethyl)benzoyl-1,2,3,4-tetrahydroquinoxalin-3-one

HRID 901964Notes

Reaction equation

HRID 901964 reaction equation
[N:1]1([C:12]([C:14]2[CH:15]=[C:16]([CH:27]=[CH:28][CH:29]=2)[CH2:17][N:18](C)[C:19](=O)OC(C)(C)C)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3](=[O:11])[CH2:2]1>Cl.O1CCOCC1.C(Cl)(Cl)Cl>[CH3:19][NH:18][CH2:17][C:16]1[CH:15]=[C:14]([CH:29]=[CH:28][CH:27]=1)[C:12]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3](=[O:11])[CH2:2]1)=[O:13]

Participants

4

Reactant 1

HCID 69208344tert-butyl N-(3-(1,2,3,4-tetrahydroquinoxalin-3-on-1-carbonyl)benzyl)-N-methylcarbamate

Product 1

HCID 858677023-(Methylaminomethyl)benzoyl-1,2,3,4-tetrahydroquinoxalin-3-oneYield 49%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of tert-butyl N-(3-(1,2,3,4-tetrahydroquinoxalin-3-on-1-carbonyl)benzyl)-N-methylcarbamate (280 mg, 0.71 mmol) in 4N hydrogen chloride/dioxan (30 ml) was stirred at room temperature for 1 h. The mixture was reduced in vacuo, taken up in chloroform, washed with saturated sodium hydrogen carbonate solution and brine, dried and reduced. Chromatography (10% methanol/90% chloroform) afforded 1-(3-(methylaminomethyl)benzoyl-1,2,3,4-tetrahydroquinoxalin-3-one (98 mg, 49%) as an orange solid.

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution and brine
  2. customdried

Sources & evidence

ORD record
ord-68a6b0b8168747a989d5252ad5938cc6
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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