1-Piperonylpiperazine → HCID 9869449, compound

HRID 1871244Notes

Reaction equation

HRID 1871244 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-ec2daae2f0c447cb9087b4d52c74955d
Source dataset
uspto-grants-2000_08
Patent number
US06103715

Reaction notes

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