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

HRID 1365146Notes

Reaction equation

HRID 1365146 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]>O1CCCC1>[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 tetrahydrofuran (5 ml) was added N-(2-methoxyethyl)methylamine (254 mg) and the reaction mixture was heated to reflux for 24 hours. The reaction mixture was reduced in vacuo and purified using flash 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 dichloromethane/methanol yielded piperazine-1-carboxylic acid (2-methoxy-ethyl)-methyl-amide, which was isolated as the hydrochloride salt.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. custompurified

Sources & evidence

ORD record
ord-b6146cfe4434405a969e0dcd4081f11d
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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