Triethylamine → 913952-86-0

HRID 2167351Notes

Reaction equation

HRID 2167351 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CCN(CC)CC.[CH2:21]([S:24](Cl)(=[O:26])=[O:25])[CH2:22][CH3:23]>C(Cl)Cl>[CH2:21]([S:24]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)(=[O:26])=[O:25])[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 46743467913952-86-0

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring ice-cold solution of tert-butyl piperazine-1-carboxylate (1, 10.0 g, 53.69 mmol) and Et3N (22.4 mL, 161.07 mmol) in CH2Cl2 (200 mL) was slowly added 1-propanesulfonyl chloride (7.65 g, 53.69 mmol). The mixture stirred at ambient temperature under an atmosphere of nitrogen for 3 h. The mixture was washed with 2 N NaOH (50 mL), 2 N HCl (50 mL), H2O (50 mL), brine (50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to afford tert-butyl 4-(propylsulfonyl)piperazine-1-carboxylate (2) as an off-white solid (15.70 g, quantitative): 1H NMR (500 MHz, CDCl3) δ 7.91 (d, J=1.7 Hz, 1H), 7.48 (d, J=1.6 Hz, 1H), 7.21 (m, 1H), 7.14 (s, 1H), 7.09 (s, 1H), 3.96 (s, 3H), 3.75 (s, 3H); MS (ESI+) m/z 293.

Workup

  1. washThe mixture was washed with 2 N NaOH (50 mL), 2 N HCl (50 mL), H2O (50 mL), brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3945ecc00d8c4ad6887e70280eb59f16
Source dataset
uspto-grants-2015_06
Patent number
US09045445B2

Reaction notes

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