2-Trifluoromethyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride → (S)-2-Trifluoromethyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

HRID 131419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131419
Cl.[F:2][C:3]([F:21])([F:20])[C:4]1[CH:19]=[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]([NH2:13])[C:6]=2[CH:5]=1.[CH3:22][O:23][CH2:24][CH2:25][C@H:26]1[CH2:31]N[CH2:29][CH2:28][NH:27]1>CS(C)=O.C1(C)C=CC=CC=1>[F:21][C:3]([F:2])([F:20])[C:4]1[CH:19]=[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[CH2:29][CH2:28][NH:27][C@@H:26]([CH2:25][CH2:24][O:23][CH3:22])[CH2:31]3)[C:6]=2[CH:5]=1

Komponenten

5

Edukt 2

HCID 210935172-Trifluoromethyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideHCID 55287560(S)-2-(2-Methoxyethyl)piperazine

Produkt 1

HCID 10250638(S)-2-Trifluoromethyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepineAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Heat a suspension of 2-trifluoromethyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride salt (626 mg) and (S)-2-(2-methoxy-ethyl)-piperazine (863 mg) in DMSO (1.42 mL DMSO per mmol of amine) and toluene (5.68 mL per mmol of amine) at reflux for 48 hours. Evaporate the toluene under vaccuo and pour the resulting solution into water (5.71 mL per mmol of amine). Purify the resulting brown solid by flash chromatography (methylene chloride/methanol (95:5) to afford the title compound as a yellow solid (499 mg, 60%): mp 71-82° C.; 1HNMR (CDCl3) δ 1.75-1.60 (m, 2H), 2.64 (dd, 1H), 3.07-2.94 (m, 4H), 3.31 (s, 3H), 3.48 (ddd, 2H), 3.78 (bs, 2H), 5.09 (s, 1H), 6.69 (dd, 1H), 6.93-6.88 (m, 2H), 7.00 (dt, 1H), 7.10 (dd, 1H), 7.57-7.50 (m, 2H); MS (ESI/pos) m/z (rel intensity) 405.3 (100).

Aufarbeitung

  1. temperatureHeat
  2. temperatureat reflux for 48 hours
  3. customEvaporate the toluene under vaccuo
  4. additionpour the resulting solution into water (5.71 mL per mmol of amine)
  5. customPurify the resulting brown solid by flash chromatography (methylene chloride/methanol (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-8e914a0764fb45dcba56f4923045cb2f
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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