Hydrochloride methanol → 3-(5-Bromo-1H-indol-1-yl)quinuclidine

HRID 1668462Notes

Reaction equation

HRID 1668462 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[C:4]([CH2:17][CH:18](OC)OC)[CH:3]=1.[ClH:23].CO>>[ClH:23].[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]([CH:9]1[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]1)[CH:18]=[CH:17]2

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 59004629N-(4-Bromo-2-(2,2-dimethoxyethyl)phenyl)-quinuclidin-3-amine

Product 2

HCID 313Hydrochloric AcidHCID 590046503-(5-Bromo-1H-indol-1-yl)quinuclidineYield 100%

Procedure

Compound 68 (137 mg, 0.371 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 HCl salt of 69 as an off-white solid (129 mg, 100%). 1H NMR (MeOD) δ 1.89-2.00 (m, 2H), 2.10-2.20 (m, 1H), 2.25-2.34 (m, 1H), 2.39-2.44 (m, 1H), 3.43-3.53 (m, 3H), 3.64-3.77 (m, 1H), 3.86-3.93 (m, 1H), 4.00-4.09 (m, 1H), 5.17-5.22 (m, 1H), 6.58 (d, 1H, J=3.4 Hz), 7.31 (dd, 1H, J=8.5, 1.8 Hz), 7.42 (d, 1H, J=8.8 Hz), 7.70 (d, 1H, J=3.5 Hz), 7.73 (d, 1H, J=1.8 Hz); ESI-MS (m/z, %): 305/307 (MH+, 100%).

Workup

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

Sources & evidence

ORD record
ord-e3aae078e22b4a4281abd818c670ba70
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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