Ammonia → HCID 9824850, compound

HRID 1735710Notes

Reaction equation

HRID 1735710 reaction equation
C1(OC)C=CC=CC=1.[CH2:9]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:10]1[CH:18]=[CH:17][C:16]2[O:15][CH2:14][O:13][C:12]=2[CH:11]=1.[Cl:25][C:26]1[C:31]2[NH:32][C:33]3[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=3[NH:35][C:36](=O)[C:30]=2[CH:29]=[CH:28][CH:27]=1.N>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl.C(O)(C)C>[Cl:25][C:26]1[C:31]2[NH:32][C:33]3[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=3[N:35]=[C:36]([N:22]3[CH2:23][CH2:24][N:19]([CH2:9][C:10]4[CH:18]=[CH:17][C:16]5[O:15][CH2:14][O:13][C:12]=5[CH:11]=4)[CH2:20][CH2:21]3)[C:30]=2[CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 7519AnisoleHCID 944261-Piperonylpiperazine2×HCID 15428875HCID 15428875, compound

Product 1

HCID 9824850HCID 9824850, compoundYield 70.5%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent3×HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of anisole (0.40 mL, 3.68 mmol) in dry toluene (2.00 mL) was added titanium tetrachloride (0.24 mL, 2.18 mmol) at room temperature under argon. The mixture was then treated with 1-piperonylpiperazine (2.07 g, 9.40 mmol) and 4-chloro-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine (0.49 g, 2.00 mmol) (Giani et al, supra) and diluted with toluene (1.00 mL). After more 1-piperonylpiperazine (1.19 g, 5.40 mmol) was added, toluene (8.00 mL) was added and the resulted reaction mixture was heated at reflux for 6 h before it was cooled to 60° C. Isopropanol (0.80 mL), celite (0.40 g) and ammonia (30%, 0.50 mL) were added sequentially and the whole mixture was filtered hot. Upon cooling to room temperature, the filtrate was concentrated in vacuo to dryness and the residue was subjected to column chromatography using ethyl acetate/hexanes (1/2) as the eluent. Thus 0.63 g (70%) of the title compound was afforded as a light yellow solid; m.p. 160°-162° C; MS 447 (M+ +1).

Workup

  1. customthe resulted reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 6 h before it
  4. filtrationthe whole mixture was filtered hot
  5. temperatureUpon cooling to room temperature
  6. concentrationthe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-8505de6268fd47aeb8f7f97a9c52153c
Source dataset
uspto-grants-1996_07
Patent number
US05538965

Reaction notes

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