Ammonium Chloride → cis-3-Benzyl-6-bromo-8-methyl-1,2,3,4,4a,9a-hexahydro-3-aza-fluoren-9-one

HRID 1714141Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16]C)=O)[CH:10]([C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([Br:25])[CH:19]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>O>[CH2:1]([N:8]1[CH2:9][C@H:10]2[C@H:11]([C:14](=[O:16])[C:23]3[C:18]2=[CH:19][C:20]([Br:25])=[CH:21][C:22]=3[CH3:24])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of methyl 1-benzyl-3-(3-bromo-5-methyl-phenyl)piperidine-4-carboxylate (12.2 g, 30.3 mmol) from step B and polyphosphoric acid (124 g) was heated at 180° C. for 3 h then cooled to 0.20° C. To the reaction mixture H2O and saturated NH4Cl aqueous solution were added, successively then extracted with EtOAc. The combined organic solution was dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed in silica gel column (Hex/EtOAc 9/1) to obtain the title compound (760 mg, 2.1 mmol): MS (ES) 370.1 (M+H).

Workup

temperaturethen cooled to 0.20° C
extractionsuccessively then extracted with EtOAc
dry with materialThe combined organic solution was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was chromatographed in silica gel column (Hex/EtOAc 9/1)

Sources & evidence

ORD record: ord-a2274898c54944458dc73cea78f94952
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795436B2

Reaction notes

Loading…