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

HRID 253027Notes

Reaction equation

HRID 253027 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 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To piperazine-1,4-dicarboxylic acid tert-butyl ester 4-nitro-phenyl ester (500 mg, 1.42 mmol) in anhydrous THF (5 mL) was added N-(2-methoxy-ethyl)methylamine (2 eq., 254 mg). The reaction mixture was refluxed overnight, then evaporated in vacuo and purified by chromatography to give 4-[(2-methoxyethyl)-methyl-carbamoyl]piperazine-1-carboxylic acid tert-butyl ester as a clear oil (304 mg, 71%). To 4-[(2-methoxyethyl)-methyl-carbamoyl]piperazine-1-carboxylic acid tert-butyl ester (304 mg, 1.01 mmol) in dichloromethane (3 mL) was added HCl (2M solution in ether), the reaction mixture stirred at rt overnight and then evaporated in vacuo to give piperazine-1-carboxylic acid (2-methoxy-ethyl)-methyl-amide as HCl salt (330 mg).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customevaporated in vacuo
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-083ce531f2084725a03e5a9a96d2c9a6
Source dataset
uspto-grants-2011_01
Patent number
US07872003B2

Reaction notes

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