1-Piperonylpiperazine → HCID 9869449, compound

HRID 482453Notes

Reaction equation

HRID 482453 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]2[S:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=O)[CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH2:20]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[C:21]1[CH:29]=[CH:28][C:27]2[O:26][CH2:25][O:24][C:23]=2[CH:22]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:19]=[CH:18][C:7]2[S:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11]([N:33]3[CH2:34][CH2:35][N:30]([CH2:20][C:21]4[CH:29]=[CH:28][C:27]5[O:26][CH2:25][O:24][C:23]=5[CH:22]=4)[CH2:31][CH2:32]3)=[CH:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 944261-PiperonylpiperazineHCID 516892Sodium BicarbonateHCID 12362917HCID 12362917, compound

Product 1

HCID 9869449HCID 9869449, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-nitro-10-oxo-dibenzo[b,f]thiepine (0.54 g, 2.00 mmol) and 1-piperonylpiperazine (2.04 g, 9.26 mmol) in toluene (15 mL) was added titanium tetrachloride (0.24 mL, 2.2 mmol) at room temperature under argon. The resulted mixture was heated at reflux for 3.5h and then cooled down to room temperature. The whole mixture was poured into a saturated sodium bicarbonate solution (50 mL). After separation, the aqueous phase was extracted with dichloromethane (2×50 mL). The combined organic solution was dried (MgSO4), filtered and concentrated in vacuo to dryness. The residue was subjected to column chromatography using ethyl acetate/hexanes (1/2) as eluent. Thus 0.161 g (17%) of the title compound was obtained as a yellow solid; m.p. 188°-190° C.; MS 474 (M+ +1).

Workup

  1. temperatureThe resulted mixture was heated
  2. customAfter separation
  3. extractionthe aqueous phase was extracted with dichloromethane (2×50 mL)
  4. dry with materialThe combined organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-fc5445b276514374a3e98af809cfb51a
Source dataset
uspto-grants-1998_08
Patent number
US05798350

Reaction notes

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