1,8-Diazabicyclo(5.4.0)undec-7-ene → 8-Chloro-11-(4-nonyl-1-piperazinyl)dibenz[b,f][1,4]oxazepine

HRID 355673Notes

Reaction equation

HRID 355673 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](Cl)=[N:10][C:4]=2[CH:3]=1.[CH2:18]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].N12CCCN=C1CCCCC2>C(#N)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]([N:30]3[CH2:31][CH2:32][N:27]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:28][CH2:29]3)=[N:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27370981-NonylpiperazineHCID 189404158,11-Dichlorodibenzo[b,f][1,4]oxazepine

Product 1

HCID 99329128-Chloro-11-(4-nonyl-1-piperazinyl)dibenz[b,f][1,4]oxazepine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of 8,11-dichlorodibenz[b,f][1,4]oxazepine (0.32 g, 1.19 mmol), 1-nonylpiperazine (0.38 g, 1.79 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.72 mL, 0.73 g, 4.77 mmol) in acetonitrile (15 mL) was heated at reflux for 6 h. After the mixture was concentrated, water (20 mL) and ethyl acetate (20 mL) were added. The two phases were separated and the aqueous phase was extracted with ethyl acetate (2×20 mL). The combined ethyl acetate solution was dried over magnesium sulfate and filtered. The filtrate was then concentrated in vacuo to dryness and the residue was subjected to column chromatography using ethyl acetate/hexane (1/2) as the eluent. The compound 8-chloro-11-(4-nonyl-1-piperazinyl)dibenz[b,f][1,4]oxazepine was obtained as a white solid (0.15 g, 28%), m.p. 64°-66° C., MS 440 (M+ +1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. concentrationAfter the mixture was concentrated
  4. additionwater (20 mL) and ethyl acetate (20 mL) were added
  5. customThe two phases were separated
  6. extractionthe aqueous phase was extracted with ethyl acetate (2×20 mL)
  7. dry with materialThe combined ethyl acetate solution was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was then concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-b813a62d14e3499daf423c279dcf902a
Source dataset
uspto-grants-1998_11
Patent number
US05834459

Reaction notes

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