Anisole → HCID 12617935, compound

HRID 1701282Notes

Reaction equation

HRID 1701282 reaction equation
C1(OC)C=CC=CC=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]2[NH:26][C:25](=O)[C:24]3=[CH:28][CH:29]=[CH:30][N:23]3[CH2:22][C:21]=2[CH:31]=1.[OH-].[NH4+]>[Ti](Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1.C(O)(C)C>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]2[N:26]=[C:25]([N:13]3[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]3)[C:24]3=[CH:28][CH:29]=[CH:30][N:23]3[CH2:22][C:21]=2[CH:31]=1

Participants

8

Reactant 4

HCID 7519AnisoleHCID 14923Ammonium HydroxideHCID 531671-Methylpiperazine2×HCID 12595985HCID 12595985, compound

Product 1

HCID 12617935HCID 12617935, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent3×HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 15 ml. of dry toluene, 1.5 ml. of anisole and 0.8 ml. of titanium tetrachloride is cooled under argon. A solution of 2.8 ml. of N-methylpiperazine in 10 ml. of toluene is added. A 1.55 g. portion of 7-chloro-5,10-dihydro-11H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one and 1.4 ml. of N-methylpiperazine are added in succession. The reaction mixture is heated at reflux for 5 hours, cooled to 60° C. and 2.2 ml. of isopropanol, 2 ml. of concentrated ammonium hydroxide and 1 g. of celite are added. After cooling to 30° C., 20 ml. of toluene are added and the mixture is filtered and washed with toluene. The toluene layer is washed twice with water, concentrated to remove the solvent and cooled. The solid is washed onto a filter with hexane, treated with 10 ml. of 1 N acetic acid and the insoluble material is collected and washed with water. The aqueous layer is treated with 10 ml. of 1 N ammonium hydroxide. The precipitate is collected, washed with water, dried in vacuo and recrystallized from ethanol, giving the desired product, m.p. 186°-188° C.

Workup

  1. additionA mixture of 15 ml
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 5 hours
  4. additionof celite are added
  5. temperatureAfter cooling to 30° C.
  6. filtrationthe mixture is filtered
  7. washwashed with toluene
  8. washThe toluene layer is washed twice with water
  9. concentrationconcentrated
  10. customto remove the solvent
  11. temperaturecooled
  12. washThe solid is washed onto
  13. filtrationa filter with hexane
  14. additiontreated with 10 ml
  15. customof 1 N acetic acid and the insoluble material is collected
  16. washwashed with water
  17. additionThe aqueous layer is treated with 10 ml
  18. customThe precipitate is collected
  19. washwashed with water
  20. customdried in vacuo
  21. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0230c32caa07414ea9cafb03d5eb986b
Source dataset
uspto-grants-1980_03
Patent number
US04192803

Reaction notes

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