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

HRID 131423Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[N:10]=[C:11]([NH2:12])[C:5]=2[CH:4]=1.[CH3:19][O:20][CH2:21][CH2:22][C@H:23]1[CH2:28]N[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>[Cl:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[N:10]=[C:11]([N:12]3[CH2:26][CH2:25][NH:24][C@@H:23]([CH2:22][CH2:21][O:20][CH3:19])[CH2:28]3)[C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Combine 2-chloro-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride (0.840 g, 3.0 mmol), (S)-2-(2-methoxy-ethyl)-piperazine (0.865 g, 6.0 mmol), N,N-diisopropylethylamine (0.53 mL, 3.0 mmol), DMSO (1.25 ml), and toluene (5.0 ml) and stir and heat the mixture at 110° C. After 46 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 0.985 g of the crude product. Silica gel chromatography, eluting with dichloromethane/methanol (90:10) gives 0.501 g of the title compound as a yellow foam: mass spectrum (ion spray): m/z=371 (M+1).

Workup

temperaturecool the mixture to ambient temperature
washWash the organic layer with 0.1N NaOH and brine
dry with materialdry (sodium sulfate)
concentrationconcentrate the organic layer to 0.985 g of the crude product
washSilica gel chromatography, eluting with dichloromethane/methanol (90:10)

Sources & evidence

ORD record: ord-849e78a2804343898143983e53edade4
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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