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Dimethyl Sulfoxide → (S)-3-Methyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

HRID 131416
Notes
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Reaction equation

HRID 131416 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5](N)[C:6]2[CH:12]=[N:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[NH:8][C:7]=2[CH:17]=1.[CH3:19][O:20][CH2:21][CH2:22][C@H:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1.C(N(CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]([N:27]3[CH2:26][CH2:25][NH:24][C@@H:23]([CH2:22][CH2:21][O:20][CH3:19])[CH2:28]3)=[N:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[NH:8][C:7]=2[CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 210935253-methyl-5H-dibenzo[b,e][1,4]diazepin-1-ylamine hydrochlorideHCID 55287560(S)-2-(2-Methoxyethyl)piperazine

Product 1

HCID 58626009(S)-3-Methyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepineYield 48%

Reagents, catalysts & solvents

2
HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Combine 3-methyl-5H-dibenzo[b,e][1,4]diazepin-1-ylamine hydrochloride (400.0 mg, 1.54 mmol), (S)-2-(2-methoxy-ethyl)-piperazine (444.2 mg, 3.08 mmol), N,N-diisopropylethylamine (199.0 mg, 1.54 mmol), DMSO (0.7 ml), and toluene (2.8 ml) and stir and heat the mixture at 110° C. After 48 hours, cool the mixture to ambient temperature and dilute with ethyl acetate. 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 257.1 mg (48%) of a yellow foam: mp=64° C. dec; mass spectrum (ion spray): m/z =433.1 (M+1).

Workup

  1. temperaturecool the mixture to ambient temperature
  2. washWash the organic layer with 0.1N NaOH and brine
  3. dry with materialDry (sodium sulfate)
  4. concentrationconcentrate the organic layer to residue
  5. customPurify the residue on silica gel

Sources & evidence

ORD record
ord-799c2269df80402989ecd0378d73e031
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07384934B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes