Triethylamine → HCID 21963416, compound

HRID 2211887Notes

Reaction equation

HRID 2211887 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[S:21][N:20]=2)[CH2:15][CH2:14]1)([O-])=O.C(N(CC)CC)C>C1COCC1.[Ni]>[S:21]1[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:19]([N:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[NH2:1])[CH2:14][CH2:15]2)=[N:20]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 21963355HCID 21963355, compound

Product 1

HCID 21963416HCID 21963416, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-{4-[3-(2-Nitro-phenyl)-propyl]-piperazin-1-yl}-1,2-benzoisothiazole (3.25 g, 8.5 mmol) was dissolved in 100 mL of THF treated with triethylamine (0.3 ml) and with wet Raney nickel (1.02 g). The resulting mixture was placed on a shaker type hydrogenator, purged with hydrogen, pressurized (29.8 psig) and shaken at room temperature for 16 hours. The resulting mixture was filtered to remove the catalyst then filtered a second time over celite before the filtrate was concentrated. The resultant solid was dried in vacuo (2.33 g, 6.61 mmol). Yield 78%; MS (APCI): 352 [M+H]+.

Workup

  1. custompurged with hydrogen
  2. filtrationThe resulting mixture was filtered
  3. customto remove the catalyst
  4. filtrationthen filtered a second time over celite before the filtrate
  5. concentrationwas concentrated
  6. customThe resultant solid was dried in vacuo (2.33 g, 6.61 mmol)

Sources & evidence

ORD record
ord-143fa1e34d63423aa3f97eff6e94cb35
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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