Formaldehyde formic acid → trans-7-bromo-6-methoxy-2-methyl-2,3,4,8,9,9a-hexahydro-4-phenyl-1H-indeno[1,7-cd]azepine hydrobromide

HRID 622068Notes

Reaction equation

HRID 622068 reaction equation
N[CH2:2]C1C2C(=C(OC)C([Br:12])=CC=2)CC1.[Br:15][C:16]1[CH2:17][CH2:18][CH:19]2[C:28]3[C:27]=1[C:26]([O:29][CH3:30])=[CH:25][N:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:23][C:22]=3[CH2:21][CH2:20]2.C(O)=O.C=O>>[BrH:12].[Br:15][C:16]1[CH2:17][CH2:18][C@@H:19]2[C:28]3[C:27]=1[C:26]([O:29][CH3:30])=[CH:25][N:24]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:23][C:22]=3[C@H:21]([CH3:2])[CH2:20]2

Participants

4

Reactant 3

HCID 18761834Formaldehyde formic acidHCID 212933141-Aminomethyl-5-bromo-4-methoxyindanHCID 704184127-bromo-6-methoxy-2,3,4,8,9,9a-hexahydro-4-phenyl-1H-indeno[1,7-cd]azepine

Product 1

HCID 86742411trans-7-bromo-6-methoxy-2-methyl-2,3,4,8,9,9a-hexahydro-4-phenyl-1H-indeno[1,7-cd]azepine hydrobromide

Procedure

Using the methods described above and starting with 1-aminomethyl-5-bromo-4-methoxyindan, 7-bromo-6-methoxy-2,3,4,8,9,9a-hexahydro-4-phenyl-1H-indeno[1,7-cd]azepine is prepared. This intermediate is N-methylated using formic acid-formaldehyde to give cis, trans-7-bromo-6-methoxy-2-methyl-2,3,4,8,9,9a-hexahydro-4-phenyl-1H-indeno[1,7-cd]azepine hydrobromide and, after demethylation using boron tribromide, cis or trans-7-bromo-6-hydroxy-2-methyl-2,3,4,8,9,9a-hexahydro-4-phenyl-1H-indeno[1,7-cd]azepine.

Workup

  1. customis prepared

Sources & evidence

ORD record
ord-0994bb731f6b4f8387a636c2c3f372a5
Source dataset
uspto-grants-1988_09
Patent number
US04769368

Reaction notes

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