1-Piperazinecarboxylic acid, ethyl ester → HCID 18918264, compound

HRID 1291824Notes

Reaction equation

HRID 1291824 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 60984Methyl bromoacetate

Product 1

HCID 18918264HCID 18918264, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-ethoxycarbonylpiperazine (20 g) and triethylamine (14.1 g) in dichloromethane (200 ml) at 0° C. was added gradually with stirring over 10-15 minutes, methyl bromoacetate (20.3 g). On completion of the addition the reaction mixture was stirred at room temperature for 2 hours, washed with water and brine, dried (MgSO4) and evaporated to yield 1-ethoxycarbonyl-4-methoxycarbonylmethylpiperazine (29.1 g) as a colourless oil: NMR (CDCl3) δ 1.28 (3H, t), 2.56 (4H, m), 3.25 (2H, s), 3.52 (4H, m), 3.72 (3H, s), 4.14 (2H, q); m/Z 231 (M+H)+.

Workup

  1. additionOn completion of the addition the reaction mixture
  2. stirringwas stirred at room temperature for 2 hours
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-ae220fc0ad1d42f89547169a0b6413fe
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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