N-(4-Bromo-2-(2,2-dimethoxyethyl)phenyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-amine → 5-Bromo-1-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1H-indole

HRID 1668476Notes

Reaction equation

HRID 1668476 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:15][CH:14]3[N:16]([CH3:17])[CH:11]([CH2:12][CH2:13]3)[CH2:10]2)=[C:4]([CH2:18][CH:19](OC)OC)[CH:3]=1>Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]([CH:9]1[CH2:15][CH:14]3[N:16]([CH3:17])[CH:11]([CH2:12][CH2:13]3)[CH2:10]1)[CH:19]=[CH:18]2

Participants

3

Reactant 1

HCID 59004631N-(4-Bromo-2-(2,2-dimethoxyethyl)phenyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-amine

Product 1

HCID 590046405-Bromo-1-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1H-indoleYield 127.1%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

Compound 83 (118 mg, 0.308 mmol) was dissolved in anhydrous 1M HCl/methanol (10 mL) in a dry argon purged flask, refluxed for 1 hour, concentrated under reduced pressure to yield a shiny brown solid, 84 (125 mg, 100%) as a 5:1 or 1:5 mixture of endo/exo stereoisomers. 1H NMR (major isomer-DMSO-d6) δ 1.85-1.96 (m, 2H), 2.15-2.26 (m, 2H), 2.31-2.40 (m, 2H), 2.66 (d, 3H, J=4.9 Hz), 2.76-2.93 (m, 2H), 3.87-3.96 (m, 2H), 4.99-5.11 (m, 1H), 6.49 (d, 1H, J=3.4 Hz), 7.24-7.34 (m, 1H), 7.49 (d, 1H, J=8.8 Hz), 7.76 (d, 1H, J=1.6 Hz), 7.79 (d, 1H, J=2.9 Hz); ESI-MS (m/z, %): 319/321 (MH+, 100%).

Workup

  1. temperaturerefluxed for 1 hour
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5ab0096c05a4b5a8b1bd65eebc6e7b2
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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