Thionyl Chloride → tert-Butyl 4-(2-chloroethyl)piperazinecarboxylate

HRID 2101495Notes

Reaction equation

HRID 2101495 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O=S(Cl)[Cl:19]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][Cl:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate

Product 1

HCID 22106269tert-Butyl 4-(2-chloroethyl)piperazinecarboxylateYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-hydroxy-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (231 mg, 1.0 mmol) in CH2Cl2 (2 mL) at 0° C. was added dropwise SOCl2 (0.15 mL, 2.0 mmol). The mixture was allowed to warm up to ambient temperature and stirred for 14 h. Volatiles were removed in vacuo and the residue partitioned between CH2Cl2 (20 mL) and saturated NaHCO3 (10 mL). The CH2Cl2 phase was dried over Na2SO4 and concentrated in vacuo to afford 4-(2-chloro-ethyl)-piperazine-1-carboxylic acid tert-butyl ester as a white solid (130 mg, 52%): ESI MS m/z 249 [C11H21ClN2O2+H]+.

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue partitioned between CH2Cl2 (20 mL) and saturated NaHCO3 (10 mL)
  3. dry with materialThe CH2Cl2 phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0aa1f9f1678346d597242908407d8d3d
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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