Triethylamine → HCID 44286533, compound

HRID 2088310Notes

Reaction equation

HRID 2088310 reaction equation
C(N(CC)CC)C.Cl.Cl.[NH2:10][C@H:11]1[CH:16]2[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]2)[CH2:12]1.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24].[I-].ClC1C=CC=C[N+]=1C>O.C(#N)C>[CH3:19][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH:10][C@H:11]1[CH:16]2[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]2)[CH2:12]1)=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 113702-Methoxybenzoic acidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride

Product 1

HCID 44286533HCID 44286533, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1.5 ml of Acetonitrile and Triethylamine (700 uL, 5.0 mmol) was added to a flask charged with (S)-(−)-3-Aminoquinuclidine dihydrochloride (199 mg, 1.0 mmol) and o-Methoxybenzoic acid (167 mg, 1.1 mmol), followed by addition of 2-Chloro-1-methyl pyridinium iodide (383 mg, 1.5 mmol) at room temperature. After stirring overnight, about 2 ml of water was added to reaction mixture to resolve a clear solution that was subsequently injected into a Preparative HPLC instrument for purification. Desired fractions were combined and concentrated under vacuum. (S)-2-methoxy-N-(quinuclidin-3-yl)benzamide (221 mg, 85% yield) was isolated as an oil. 1H NMR (400 MHz, Methanol-D4) δ (ppm): 7.79 (dd, J=7.7 1.6 Hz, 1H), 7.51 (td, J=8.0, 1.6 Hz, 1H), 7.15 (d, J=8.5 Hz, 1H), 7.06 (t, J=7.4 Hz, 1H), 4.45 (m, 4H), 3.97 (s, 3H), 3.82 (ddd, J=11.7, 9.9, 2.0 Hz 1H), 3.37 (m, 4H), 2.37 (q, J=3.2 Hz, 1H), 2.20 (m, 1H), 2.09 (m, 2H), 1.99 (m, 1H). LCMS (ESI): m/z 261.1 (M+H [C15H20N2O]=261.15).

Workup

  1. customwas subsequently injected into a Preparative HPLC instrument for purification
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c5e1e834057043c6835719168ec5692c
Source dataset
uspto-grants-2013_05
Patent number
US08435762B2

Reaction notes

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