1-Chloroethyl chloroformate → (2S)-1-Methyl-2-[2-(methylsulfanyl)ethyl]piperazine

HRID 131390Notes

Reaction equation

HRID 131390 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[C@@H:10]([CH2:15][CH2:16][S:17][CH3:18])[CH2:9]1)C1C=CC=CC=1.Cl[C:20](OC(Cl)C)=[O:21]>ClCCCl>[NH3:8].[CH3:20][OH:21].[CH3:14][N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]1[CH2:15][CH2:16][S:17][CH3:18]

Participants

5

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 58626059(S)-4-Benzyl-1-methyl-2-(2-methylsulfanyl-ethyl)-piperazine

Product 2

HCID 21705897Ammonia methanolHCID 45099614(2S)-1-Methyl-2-[2-(methylsulfanyl)ethyl]piperazineYield 118.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a cold solution of (S)-4-benzyl-1-methyl-2-(2-methylsulfanyl-ethyl)-piperazine (0.450 g, 1.7 mmol) in 1,2-dichloroethane (5.0 mL) is added dropwise 1-chloroethyl chloroformate (0.24 mL, 2.2 mmol). After stirring at ambient temperature for 18 hours, the 1,2-dichloroethane is evaporated and 40 mL of methanol is added to the residue. This solution is refluxed for 2 hours. Evaporation of the methanol gives the crude product. Silica gel chromatography, eluting with methylene chloride:2N ammonia/methanol (90:10), gives 0.175 g of the title compound as a light yellow oil; mass spectrum (ion spray): m/z=175 (M+1).

Workup

  1. customthe 1,2-dichloroethane is evaporated
  2. addition40 mL of methanol is added to the residue
  3. temperatureThis solution is refluxed for 2 hours
  4. customEvaporation of the methanol
  5. customgives the crude product
  6. washSilica gel chromatography, eluting with methylene chloride

Sources & evidence

ORD record
ord-82aa3edd489a4eaab94e85b3ba1aa991
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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