Hydrochloric Acid → HCID 68731830, compound

HRID 1972315Notes

Reaction equation

HRID 1972315 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-401940cd5f35412fa810e5b793972801
Source dataset
uspto-grants-2013_04
Patent number
US08431694B1

Reaction notes

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