Dimethyl Sulfide → 3-(3,5-Difluorophenyl)-2-[2'-(3-methoxypropyl)-3-methylbiphenyl-4-yl]propan-1-amine

HRID 2194926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194926
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:15][C:14]=2[CH3:30])[C:11]#[N:12])[CH:5]=[C:6]([F:8])[CH:7]=1.CSC>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:15][C:14]=2[CH3:30])[CH2:11][NH2:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Komponenten

4

Edukt 2

HCID 1068Dimethyl SulfideHCID 674487153-(3,5-Difluorophenyl)-2-[2'-(3-methoxypropyl)-3-methylbiphenyl-4-yl]propanenitrile

Produkt 1

HCID 584884533-(3,5-Difluorophenyl)-2-[2'-(3-methoxypropyl)-3-methylbiphenyl-4-yl]propan-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(3,5-difluorophenyl)-2-[2′-(3-methoxypropyl)-3-methylbiphenyl-4-yl]propanenitrile from step 3 (1 eq.) in THF (0.1M) was added borane-dimethyl sulfide complex (5 eq.). The mixture was refluxed for 5 h without a condensor to release the dimethylsulfide. The final concentration was 0.2M. The mixture was cooled to room temperature, quenched slowly with HCl (1N). The pH was set to 10 using NaOH (1N) and finally the mixture was extracted with CH2Cl2. The organic extract was dried over Na2SO4 filtered and concentrated. Purification by column chromatography on silica gel eluting with CH2Cl2/MeOH(NH3; 2M) 5% afforded the desired compound as a colorless oil. 1H NMR (500 MHz, CD3OD): δ 7.42 (d, 1H), 7.30-7.26 (m, 2H), 7.23-7.20 (m, 2H), 7.12 (d, 1H), 7.04 (s, 1H), 6.76-6.72 (m, 1H), 6.66-6.63 (m, 2H), 3.53-3.50 (m, 1H), 3.25-3.20 (m, 7H), 3.15 (dd, 1H), 2.88 (dd, 1H), 2.65 (d, 1H), 2.64 (d, 1H), 2.12 (s, 3H), 1.70-1.65 (m, 2H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 5 h without a condensor
  2. customquenched slowly with HCl (1N)
  3. extractionfinally the mixture was extracted with CH2Cl2
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel eluting with CH2Cl2/MeOH(NH3; 2M) 5%

Quellen und Nachweise

ORD-Eintrag
ord-7d9f6ef02cba4365adfc558700baadf1
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334308B2

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