Triethylamine → HCID 58561856, compound

HRID 2167355Notes

Reaction equation

HRID 2167355 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.[CH3:21][N:22]1[CH:26]=[C:25]([S:27](Cl)(=[O:29])=[O:28])[N:24]=[CH:23]1>C(Cl)Cl.CCOCC>[CH3:21][N:22]1[CH:26]=[C:25]([S:27]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)(=[O:29])=[O:28])[N:24]=[CH:23]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27368871-methyl-1H-imidazole-4-sulfonyl chloride

Product 1

HCID 58561856HCID 58561856, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred ice-cold solution of tert-butyl piperazine-1-carboxylate (C1, 10.0 g, 53.76 mmol) in CH2Cl2 (50 mL) at 0° C. was added Et3N (22.66 mL, 161.29 mmol) and a solution of 1-methyl-1H-imidazole-4-sulfonyl chloride (11.61 g, 64.51 mmol) in CH2Cl2 (50 mL) drop wise over 30 minutes while maintaining the temperature of the reaction mixture below 5° C. and under an atmosphere of N2. The reaction mixture was warmed to room temperature and stirred for an additional 5 h then quenched with a saturated solution of NaHCO3 (50 mL). The aqueous mixture was extracted with CH2Cl2 (3×100 mL), and the combined organic extracts were washed with brine (1×50 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give a crude solid. The solids were suspended in Et2O and stirred for 30 minutes at room temperature then filtered, washed with cold diethyl ether and dried under vacuum to afford tert-butyl 4-(1-methyl-1H-imidazol-4-ylsulfonyl)piperazine-1-carboxylate (36) as an off-white solid (16.8, 95%): 1H NMR (300 MHz, CDCl3) δ (dd, J=1.5 Hz, 14.56 Hz, 2H), 3.76 (s, 3H), 3.55-3.45 (m, 4H), 3.20-3.10 (m, 4H), 1.43 (s, 9H); MS (ESI+) m/z 331 (M+H).

Workup

  1. customthen quenched with a saturated solution of NaHCO3 (50 mL)
  2. extractionThe aqueous mixture was extracted with CH2Cl2 (3×100 mL)
  3. washthe combined organic extracts were washed with brine (1×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a crude solid
  8. stirringstirred for 30 minutes at room temperature
  9. filtrationthen filtered
  10. washwashed with cold diethyl ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-d003982e10d1462da5dce92118523abe
Source dataset
uspto-grants-2015_06
Patent number
US09045445B2

Reaction notes

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