Triethylamine → 4-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine

HRID 2211858Notes

Reaction equation

HRID 2211858 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[S:20][N:19]=3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-])=O.C(N(CC)CC)C>C1COCC1.[Ni]>[S:20]1[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:18]([N:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=3)[CH2:17][CH2:16]2)=[N:19]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 219632673-{4-[2-(4-Nitro-phenyl)-ethyl]-piperazin-1-YL}-1,2-benzisothiazole

Product 1

HCID 219631764-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamineYield 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-{4-[2-(4-Nitro-phenyl)-ethyl]-piperazin-1-yl}-1,2-benzisothiazole (942 mg, 2.56 mmol) was dissolved in 50 mL of THF treated with triethylamine (0.3 mL) and with wet Raney nickel (0.14 g). The resulting mixture was placed on a shaker type hydrogenator, purged with hydrogen, pressurized (two re-pressurizations were needed to maintain the pressure between 3 and 17 psig) and shaken at room temperature for 64 hours. The resulting mixture was filtered to remove the catalyst then filtered a second time over celite before the filtrate was concentrated. The resultant white solid was dried in vacuo (830 mg, 2.45 mmol). Yield 96%; mp 154° C.; MS (APCI): 339 [M+H]+.

Workup

  1. custompurged with hydrogen
  2. temperatureto maintain the pressure between 3 and 17 psig) and
  3. filtrationThe resulting mixture was filtered
  4. customto remove the catalyst
  5. filtrationthen filtered a second time over celite before the filtrate
  6. concentrationwas concentrated
  7. customThe resultant white solid was dried in vacuo (830 mg, 2.45 mmol)

Sources & evidence

ORD record
ord-839737a5cd5f456bb51aecf56a8a43ba
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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