Dimethyl Sulfoxide → 11-{(S)-3-[2-(3-Fluoro-phenyl)-ethyl]-piperazin-1-yl}-3-methyl-5H-dibenzo[b,e][1,4]diazepine

HRID 1350512Notes

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.[F:19][C:20]1[CH:21]=[C:22]([CH2:26][CH2:27][C@H:28]2[CH2:33][NH:32][CH2:31][CH2:30][NH:29]2)[CH:23]=[CH:24][CH:25]=1.C(N(CC)C(C)C)(C)C.CS(C)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1>[F:19][C:20]1[CH:21]=[C:22]([CH2:26][CH2:27][C@@H:28]2[NH:29][CH2:30][CH2:31][N:32]([C:12]3[C:6]4[CH:5]=[CH:4][C:3]([CH3:2])=[CH:17][C:7]=4[NH:8][C:9]4[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=4[N:11]=3)[CH2:33]2)[CH:23]=[CH:24][CH:25]=1

Participants

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-(3-Fluoro-phenyl)-ethyl]-piperazine (641.5 mg, 3.08 mmol), N,N-diisopropylethylamine (199.0 mg, 1.54 mmol), DMSO (0.7 ml), and toluene (2.8 ml). Stir and heat the mixture at 110° C. After 64 hours, cool the mixture to ambient temperature and then dilute it with ethyl acetate. Wash the organic layer with 0.1 N 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 423.2 mg (66%) of a tan foam: mp 81°, dec; mass spectrum (ion spray): m/z 415.2 (M+1).

Workup

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

Sources & evidence

ORD record: ord-f5bdfd117ce349e2bd6c4dc66c901cbc
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214673B2

Reaction notes

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