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

HRID 11219

Reaction equation

[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

Participants

Conditions

Temperature: 65 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-7c45a7a9c1bb48d9913c24128571cdaf
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098203B2

Linked notes

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