Formic Acid → 4-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-1-methyl-4-phenylazepane

HRID 11219

Reaktionsgleichung

Reaktionsgleichung von HRID 11219
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C=O.[CH:33](O)=O>C(Cl)(Cl)Cl>[F:30][C:2]([F:29])([F:1])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:15][CH2:14][CH2:13][N:12]([CH3:33])[CH2:11][CH2:10]1

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 116261604-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane

Produkt 1

HCID 219731264-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-1-methyl-4-phenylazepaneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

The mixture of Isomer A of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane (3 mg), paraformaldehyde (3 mg) and formic acid (2.2 mg) in chloroform (0.1 mL) was stirred at 65° C. for overnight. After cooling down, the mixture was concentrated under vacuum and filtered through anion exchange cartridge to get rid of formic acid. The crude product was purified by prep TLC with 10% methanol/89% dichloromethane/1% NH4OH to give the product as a clear sticky oil (2 mg, 67% yield).

Aufarbeitung

  1. temperatureAfter cooling down
  2. concentrationthe mixture was concentrated under vacuum
  3. filtrationfiltered through anion exchange cartridge
  4. customto get rid of formic acid
  5. customThe crude product was purified by prep TLC with 10% methanol/89% dichloromethane/1% NH4OH

Quellen und Nachweise

ORD-Eintrag
ord-7c45a7a9c1bb48d9913c24128571cdaf
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098203B2

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