(2-Methoxyethyl)(methyl)amine → 4-[(2-Methoxyethyl)-methyl-carbamoyl]piperazine-1-carboxylic acid tert-butyl ester

HRID 2353110Notes

Reaction equation

HRID 2353110 reaction equation
[N+](C1C=CC(O[C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[O:12])=CC=1)([O-])=O.[CH3:26][O:27][CH2:28][CH2:29][NH:30][CH3:31]>C1COCC1>[C:22]([O:21][C:19]([N:16]1[CH2:15][CH2:14][N:13]([C:11](=[O:12])[N:30]([CH2:29][CH2:28][O:27][CH3:26])[CH3:31])[CH2:18][CH2:17]1)=[O:20])([CH3:23])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 22462238HCID 22462238, compound

Product 1

HCID 574939694-[(2-Methoxyethyl)-methyl-carbamoyl]piperazine-1-carboxylic acid tert-butyl esterYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To piperazine-1,4-dicarboxylic acid tert-butyl ester 4-nitro-phenyl ester (500 mg) in THF (5 mL) was added N-(2-methoxyethyl)methylamine (254 mg) and the reaction mixture was heated to reflux for 24 h. The reaction mixture was concentrated in vacuo and purified using flash column chromatography to yield 4-[(2-methoxy-ethyl)-methyl-carbamoyl]-piperazine-1-carboxylic acid tert-butyl ester (304 mg). Treatment of this compound with HCl in DCM/MeOH yielded the desired compound, which was isolated as the hydrochloride salt.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 24 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified

Sources & evidence

ORD record
ord-921bef0f4d3247e5b646ba274c0e2409
Source dataset
uspto-grants-2010_07
Patent number
US07750002B2

Reaction notes

Loading…