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Dimethyl Sulfoxide → 3-Methyl-11-(4-methyl-piperazin-1-yl)-3-methyl-5H-dibenzo[b,e][1,4]diazepine

HRID 1350509
Notes
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Reaction equation

HRID 1350509 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]([NH2:13])=[N:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7]=2[CH:18]=1.[CH3:19][N:20]1[CH2:25][CH2:24]N[CH2:22][CH2:21]1.[CH:26](N(CC)C(C)C)(C)C.CS(C)=O>Cl.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:2][C:3]1([CH3:26])[CH:18]=[C:7]2[NH:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[N:11]=[C:12]([N:13]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[C:6]2=[CH:5][CH2:4]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 210935233-Methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride

Product 1

HCID 694899693-Methyl-11-(4-methyl-piperazin-1-yl)-3-methyl-5H-dibenzo[b,e][1,4]diazepineYield 42%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Combine 3-methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride (636.4 mg, 2.85 mmol), N-methylpiperazine (444.2 mg, 3.08 mmol), N,N-diisopropylethylamine (856.5 mg, 8.55 mmol), DMSO (2.0 ml), and toluene (4.0 ml). Stir and heat the mixture at 110° C. After 48 hours, add one drop of 5N HCl. After 72 hours, cool the mixture to ambient temperature and then dilute it with ethyl acetate. Wash the organic layer with DI H2O 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 362.9 mg (42%) of a tan foam: mp 84°, dec; mass spectrum (ion spray): m/z=307.1 (M+1).

Workup

  1. waitAfter 72 hours
  2. temperaturecool the mixture to ambient temperature
  3. washWash the organic layer with DI H2O 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-21e08f58f120417ab45618e4052d5917
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07214673B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes