2-(4-Methoxyphenyl)propan-1-amine → N-(2-Chloro-3-trifluoromethylbenzyl)-2-(4-methoxyphenyl)propylamine

HRID 902741

Reaktionsgleichung

Reaktionsgleichung von HRID 902741
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:12])[CH2:10][NH2:11])=[CH:5][CH:4]=1.[Cl:13][C:14]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.CCOCC>[Cl:13][C:14]1[C:21]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH:11][CH2:10][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:12]

Komponenten

6

Edukt 3

HCID 2026252-(4-Methoxyphenyl)propan-1-amineHCID 521998p-Toluenesulfonic acid monohydrateHCID 27366722-Chloro-3-(trifluoromethyl)benzaldehyde

Produkt 1

HCID 69254854N-(2-Chloro-3-trifluoromethylbenzyl)-2-(4-methoxyphenyl)propylamineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 2-(4-methoxyphenyl)propylamine (183 mg, 1.11 mmole) and 2-chloro-3-trifluoromethylbenzaldehyde (230 mg, 1.11 mmole) in 10 mL of MeOH was treated with a crystal of p-toluenesulfonic acid hydrate, and stirred for 30 minutes. The reaction was diluted with Et2O, and washed with aqueous NaHCO3. The extracts were dried, and the solvent removed. A solution of the residue in 10 mL of MeOH was cooled to 0° and treated with excess NaBH4. The reaction was warmed to 23° and stirred for 30 minutes. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried and the solvent removed, and gave the titled compound, 305 mg (77% yield). MS (ESI) 358 (MH+)

Aufarbeitung

  1. washwashed with aqueous NaHCO3
  2. customThe extracts were dried
  3. customthe solvent removed
  4. temperatureA solution of the residue in 10 mL of MeOH was cooled to 0°
  5. additiontreated with excess NaBH4
  6. temperatureThe reaction was warmed to 23°
  7. stirringstirred for 30 minutes
  8. additionThe reaction was diluted with H2O
  9. extractionextracted with Et2O
  10. washThe extracts were washed with H2O
  11. customdried
  12. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-186c9854a9884c8eb685c624d6261659
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365085B2

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