1-Piperonylpiperazine → HCID 9869449, compound

HRID 1735711Notes

Reaction equation

HRID 1735711 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 3.5 h 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. temperatureat reflux for 3.5 h
  3. customAfter separation
  4. extractionthe aqueous phase was extracted with dichloromethane (2×50 mL)
  5. dry with materialThe combined organic solution was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-c30135ca8f83458dbdd87be0b8cb2fc6
Source dataset
uspto-grants-1996_07
Patent number
US05538965

Reaction notes

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