Methyl chloroformate → 1-Carbomethoxy-4-benzylpiperazine

HRID 1731995Notes

Reaction equation

HRID 1731995 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:15]([O:17][CH3:18])=[O:16].[OH-].[Na+]>C(Cl)(Cl)Cl.O>[C:15]([N:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1)([O:17][CH3:18])=[O:16]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 759941-Benzylpiperazine

Product 1

HCID 32977831-Carbomethoxy-4-benzylpiperazineYield 81.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 35.2 g (0.20 mole) of 1-benzylpiperazine in 100 ml of CHCl3 was added dropwise over a period of 30 minutes a solution of 17.0 g (0.18 mole) of methyl chloroformate in 110 ml of CHCl3. The mixture was allowed to reflux during 2.5 hours and was made basic with 16 g of sodium hydroxide in 100 ml of water. The nonaqueous layer was separated, dried over magnesium sulphate and concentrated. The residue was distilled b.p. 108°-10° C. at 0.1-0.2 mmHg to give 34.5 g of 1-carbomethoxy-4-benzylpiperazine.

Workup

  1. temperatureto reflux during 2.5 hours
  2. customThe nonaqueous layer was separated
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. distillationThe residue was distilled b.p. 108°-10° C. at 0.1-0.2 mmHg

Sources & evidence

ORD record
ord-999c0488deda4291bdc6f2e48d05b280
Source dataset
uspto-grants-1986_11
Patent number
US04624953

Reaction notes

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