2-(Quinuclidin-3-yl)acetic acid → N-(2-(3-methoxyphenyl)propan-2-yl)-2-(quinuclidin-3-yl)acetamide

HRID 2281274Notes

Reaction equation

HRID 2281274 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.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:21]([NH2:24])([CH3:23])[CH3:22])[CH:18]=[CH:19][CH:20]=1>>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:21]([NH:24][C:10](=[O:12])[CH2:9][CH:3]2[CH:4]3[CH2:5][CH2:6][N:1]([CH2:8][CH2:7]3)[CH2:2]2)([CH3:22])[CH3:23])[CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 103521012-(Quinuclidin-3-yl)acetic acidHCID 139113102-(3-Methoxyphenyl)-2-propanamine

Product 1

HCID 68327907N-(2-(3-methoxyphenyl)propan-2-yl)-2-(quinuclidin-3-yl)acetamideYield 40%

Procedure

Using general procedure I, 2-(quinuclidin-3-yl)acetic acid (169 mg, 1.00 mmol) and 2-(3-methoxyphenyl)propan-2-amine (182 mg, 1.10 mmol) gave the title compound as a white solid (126 mg, 40%). 1H NMR (400 MHz, CDCl3) δ 7.39 (s, 1H), 7.20 (t, J=8.0 Hz, 1H), 6.92 (d, J=8.0 Hz, 1H), 6.87 (d, J=2.0 Hz, 1H), 6.71 (dd, J=8.0, 2.0 Hz, 1H), 3.75 (s, 3H), 3.31-3.42 (m, 2H), 3.00-3.19 (m, 4H), 2.47-2.60 (m, 2H), 2.27 (dd, J=14.0, 6.0 Hz, 1H), 1.83-2.06 (m, 4H), 1.64-1.74 (m, 1H), 1.61 (d, J=12.4 Hz, 6H) ppm. 13C NMR (400 MHz, CDCl3) δ 170.0, 159.7, 149.3, 129.5, 117.5, 111.8, 111.0, 55.9, 55.4, 52.0, 50.6, 46.6, 46.0, 39.7, 30.9, 29.7, 29.1, 24.3, 18.8 ppm. Purity: 93.7% HPLCMS (210 nm); retention time 0.76 min; (M+1) 317.

Sources & evidence

ORD record
ord-4adaae8efabf4f34887f7c9ea2ae558f
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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