2-(Quinuclidin-3-yl)acetic acid → 2-(1-aza-bicyclo[2.2.2]oct-3-yl)-N-[1-(3-isopropyl-phenyl)-1-methyl-ethyl]-acetamide

HRID 2281276Notes

Reaction equation

HRID 2281276 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([CH2:9][C:10]([OH:12])=O)[CH2:2]2.[CH:13]([C:16]1[CH:17]=[C:18]([C:22]([NH2:25])([CH3:24])[CH3:23])[CH:19]=[CH:20][CH:21]=1)([CH3:15])[CH3:14]>>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([CH2:9][C:10]([NH:25][C:22]([C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH:13]([CH3:15])[CH3:14])[CH:17]=1)([CH3:24])[CH3:23])=[O:12])[CH2:2]2

Participants

3

Reactant 2

HCID 103521012-(Quinuclidin-3-yl)acetic acidHCID 208115131-Methyl-1-[3-(1-methylethyl)phenyl]ethylamine

Product 1

HCID 903862222-(1-aza-bicyclo[2.2.2]oct-3-yl)-N-[1-(3-isopropyl-phenyl)-1-methyl-ethyl]-acetamideYield 10%

Procedure

Using general procedure I, (1-aza-bicyclo[2.2.2]oct-3-yl)-acetic acid (200 mg, 1.20 mmol) and 1-(3-isopropyl-phenyl)-1-methyl-ethylamine gave the title compound as a white solid (42 mg, 10%). 1H NMR (400 MHz, DMSO-d) δ 7.15-1.20 (m, 3H), 7.05 (d, J=8.4 Hz, 1H), 3.41-3.45 (m, 1H), 3.26 (s, 2H), 3.15-3.22 (m, 2H), 2.71-2.82 (m, 2H), 2.41-2.47 (m, 3H), 2.05-2.12 (m, 1H), 1.79-1.90 (m, 4H), 1.61 (d, J=8.0 Hz, 6H), 1.21 (d, J=6.4 Hz, 6H) ppm. 13C NMR (400 MHz, DMSO-d) δ 171.1, 148.7, 147.3, 128.1, 123.9, 122.8, 122.2, 55.6, 52.1, 46.5, 45.9, 38.8, 34.5, 30.7, 28.9, 28.5, 23.8, 23.4, 18.0 ppm. Purity: 96.8% HPLCMS (210 nm); retention time 1.93 min; (M+1) 329.

Sources & evidence

ORD record
ord-4379a8fe019543489e64522c08054228
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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