Cyclopropylamine → N-(3,3-bis(4-fluorophenyl)propyl)cyclopropanamine

HRID 2190350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190350
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH:10]=O)=[CH:4][CH:3]=1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH2:10][NH:22][CH:19]2[CH2:21][CH2:20]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 183626473,3-Bis(4-fluorophenyl)propanal

Produkt 1

HCID 57586327N-(3,3-bis(4-fluorophenyl)propyl)cyclopropanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To solution of 3,3-bis(4-fluorophenyl)propanal (1.00 g, 4.06 mmol, see Method H for preparation) in MeOH (15 ml) was added cyclopropanamine (0.285 ml, 4.06 mmol). The reaction mixture was stirred for overnight at 25° C. Sodium borohydride (0.307 g, 8.12 mmol) was carefully added to the reaction mixture over 15 min. After stirring an additional 15 min volatiles were removed by concentration under reduced pressure. The leftover residue was solubilized with 60 mL of a 1:2 mixture of 10% NaOH and ethyl acetate. The organic phase was separated and the aqueous phase was extracted further with ethyl acetate (2×40 mL). Purification by chromatography on silica (eluted with 0->10% MeOH/CH2Cl2+0->1% NH4OH) gave N-(3,3-bis(4-fluorophenyl)propyl)cyclopropanamine 181. The product was dissolved in CH2Cl2 and made into the HCl salt by precipitation with etheral HCl and then concentration of volatiles.

Aufarbeitung

  1. stirringAfter stirring an additional 15 min volatiles
  2. customwere removed by concentration under reduced pressure
  3. additionThe leftover residue was solubilized with 60 mL of a 1:2 mixture of 10% NaOH and ethyl acetate
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted further with ethyl acetate (2×40 mL)
  6. customPurification by chromatography on silica (eluted with 0->10% MeOH/CH2Cl2+0->1% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-6c5cd7f7ce3642f7be43918c7b506a45
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324396B2

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