Triethylamine → HCID 66751339, compound

HRID 534921Notes

Reaction equation

HRID 534921 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].C(N(CC)CC)C.Cl[C:27]([O:29][CH2:30][C:31]([Cl:34])([Cl:33])[Cl:32])=[O:28]>O1CCCC1>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:27]([O:29][CH2:30][C:31]([Cl:34])([Cl:33])[Cl:32])=[O:28])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66751339HCID 66751339, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (4.00 g, 3.43 mmol), and triethylamine (4.43 g, 43.8 mmol) in tetrahydrofuran (70 mL) was added 2,2,2-trichloroethyl chloroformate (3.06 g, 14.4 mmol) and the mixture was stirred at room temperature for 48 h. The reaction mixture was partitioned between ethyl acetate and water, and the organic layer was washed with water, saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was filtered through a pad of silica gel eluted with ethyl acetate to afford a white solid. The solid was triturated with hexane to give the title compound (2.54 g, 47%) as a white solid.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with water, saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe resulting residue was filtered through a pad of silica gel
  7. washeluted with ethyl acetate
  8. customto afford a white solid
  9. customThe solid was triturated with hexane

Sources & evidence

ORD record
ord-06883e50da4f4068ba6e900a109df4f2
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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