Dimethyl Sulfoxide → 11-(4-Methyl-1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepine

HRID 1350517Notes

Reaction equation

HRID 1350517 reaction equation
Cl.[CH:2]1[C:12]2[C:11]([NH2:13])=[N:10][C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=3[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:18][N:19]1[CH2:24][CH2:23]N[CH2:21][CH2:20]1.C(N(CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:18][N:19]1[CH2:24][CH2:23][N:13]([C:11]2[C:12]3[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=3[NH:7][C:8]3[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=3[N:10]=2)[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 21093534HCID 21093534, compound

Product 1

HCID 1610311-(4-Methyl-1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepineYield 45%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride (600.0 mg, 2.44 mmol), N-methylpiperazine (1.47 g, 14.65 mmol), N,N-diisopropylethylamine (315.6 mg, 2.44 mmol), DMSO (1.0 ml), and toluene (4.0 ml). Stir and beat the mixture at 110° C. After 21 hours, cool the mixture to ambient temperature and stir it overnight. Dilute the mixture with ethyl acetate and wash the organic layer with 0.1N NaOH and brine. Dry (sodium sulfate) and concentrate the organic layer to residue. Purify the residue on silica gel using dichloromethane/methanol (90:10) to give 319.7 mg (45%) of a tan foam: mp 173° C. –179° C., dec; mass spectrum (ion spray): m/z=293.1 (M+1).

Workup

  1. customat 110° C
  2. stirringstir it overnight
  3. washwash the organic layer with 0.1N NaOH and brine
  4. dry with materialDry (sodium sulfate)
  5. concentrationconcentrate the organic layer to residue
  6. customPurify the residue on silica gel

Sources & evidence

ORD record
ord-51c28ecac6fa410fb476e16f384385b1
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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