2-(Quinuclidin-3-yl)acetic acid → 2-(quinuclidin-3-yl)-N-(1-p-tolylcyclopropyl)acetamide

HRID 2281273Notes

Reaction equation

HRID 2281273 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.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([C:19]2([NH2:22])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1>>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([CH2:9][C:10]([NH:22][C:19]1([C:16]3[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=3)[CH2:20][CH2:21]1)=[O:12])[CH2:2]2

Participants

3

Reactant 2

HCID 103521012-(Quinuclidin-3-yl)acetic acidHCID 129831461-(p-Tolyl)cyclopropanamine

Product 1

HCID 683277552-(quinuclidin-3-yl)-N-(1-p-tolylcyclopropyl)acetamideYield 20.1%

Procedure

Using general procedure I, 2-(quinuclidin-3-yl)acetic acid (169 mg, 1.00 mmol) and 1-p-tolylcyclopropanamine (149 mg, 1.10 mmol) gave the title compound as a white solid (60 mg, 18%). 1H NMR (400 MHz, CDCl3) δ 7.86 (s, 1H), 6.96-7.07 (m, 4H), 3.22-3.37 (m, 2H), 2.85-3.05 (m, 4H), 2.39-2.45 (m, 2H), 2.21 (s, 3H), 1.45-1.92 (m, 5H), 1.07-1.23 (m, 5H) ppm. 13C NMR (400 MHz, CDCl3) δ 171.6, 139.8, 136.1, 129.2, 125.6, 52.1, 50.9, 46.5, 46.0, 39.2, 34.9, 30.8, 24.5, 21.1, 18.7, 17.6 ppm. Purity: 96.2% HPLCMS (210 nm); retention time 1.21 min; (M+1) 299.

Sources & evidence

ORD record
ord-4fbf7ffd5b3c4cc5a94f6212366565ee
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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