2,2,2-Trichloroethyl chloroformate → HCID 21187589, compound

HRID 1383331Notes

Reaction equation

HRID 1383331 reaction equation
C[N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[C:11]([CH3:17])[NH:12]3)[CH2:4][CH2:3]1.Cl[C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20].C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:24][C:23]([Cl:26])([Cl:25])[CH2:22][O:21][C:19]([N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH:10]=[C:11]([CH3:17])[NH:12]3)[CH2:4][CH2:3]1)=[O:20]

Participants

5

Reactant 3

HCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 15550247HCID 15550247, compound

Product 1

HCID 21187589HCID 21187589, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-methyl-1-(2-methyl-1H-indol-4-yl)piperazine (0.510 g, 2.22 mmol) and 2,2,2-trichloroethyl chloroformate (5 mL) was heated at 100-110° C. for 48 hours. The reaction solution was cooled, and methylene chloride (200 mL) followed carefully by a saturated solution of sodium hydrogen carbonate (20 mL) were added. The organic layer was removed, dried (potassium carbonate), and evaporated under reduced pressure. The residue was chromatographed using silica gel (approximately 300 g) using elution with 10% ethyl acetate in hexanes to afford 4-(2,2,2-trichloroethoxycarbonyl)-1-(2-methyl-1H-indol-4-yl)piperazine as a white amorphous solid (0.74 g, 1.89 mmol, 85%): FAB LRMS (m/z, relative intensity) 394 (9), 392 (27), 390 ([MH+ with 35Cl], 32), 358 (18), 356 (29), 216 (99), 194 (100). This compound was used directly as outlined below.

Workup

  1. temperatureThe reaction solution was cooled
  2. additionwere added
  3. customThe organic layer was removed
  4. dry with materialdried (potassium carbonate)
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed
  7. washelution with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-dc3d595350924e46b0b15a041383d9d2
Source dataset
uspto-grants-2001_07
Patent number
US06255306B1

Reaction notes

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