Hydrochloric Acid → HCID 68731830, compound

HRID 1805791Notes

Reaction equation

HRID 1805791 reaction equation
[ClH:1].[CH3:2][S:3]([N:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)(=[O:5])=[O:4]>O1CCOCC1.C(Cl)Cl>[Cl-:1].[CH3:2][S:3]([N:6]1[CH2:11][CH2:10][NH2+:9][CH2:8][CH2:7]1)(=[O:5])=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 4496004Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate

Product 1

HCID 68731830HCID 68731830, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A 4M hydrogen chloride solution in 1,4-dioxane (1.2 L) was added slowly to a cold solution of tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylate 7 (105 g) in methylene chloride (1.1 L) while maintaining the internal temperature below 20° C. The solution was stirred for 20 hours and 1H NMR indicated that the reaction was complete. The resulting slurry was filtered and rinsed with methylene chloride (300 ml). The cake was dried in a vacuum oven at 50° C. for 20 hours to afford 4-(methylsulfonyl)piperazin-1-ium chloride 8 as a white solid (78.4 g, 97% yield over 2 steps). 1H NMR (400 MHz, CDCl3) δ 3.00 (s, 3H), 3.17 (m, 4H), 3.38 (m, 4H), 9.45 (br s, 2H).

Workup

  1. temperaturewhile maintaining the internal temperature below 20° C
  2. filtrationThe resulting slurry was filtered
  3. washrinsed with methylene chloride (300 ml)
  4. customThe cake was dried in a vacuum oven at 50° C. for 20 hours

Sources & evidence

ORD record
ord-fad2445b3c0c4f979f02850eaec9558f
Source dataset
uspto-grants-2013_01
Patent number
US08354528B2

Reaction notes

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