Triethylamine → HCID 59331199, compound

HRID 2088311Notes

Reaction equation

HRID 2088311 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.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24]([C:27](O)=[O:28])=[CH:23][CH:22]=1.[I-].ClC1C=CC=C[N+]=1C>O.C(#N)C>[N:13]12[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]1)[C@H:11]([NH:10][C:27](=[O:28])[C:24]1[CH:25]=[CH:26][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:22][CH:23]=1)[CH2:12]2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 99664-(Trifluoromethyl)benzoic acidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride

Product 1

HCID 59331199HCID 59331199, compoundYield 93.2%

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 α,α,α-Trifluoro-p-toluic acid (209 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, concentrated under vacuum, and then recrystallized from 4 mL of Methanol/water (3:2) to isolate white crystalline solid of (S)—N-(quinuclidin-3-yl)-4-(trifluoromethyl)benzamide (278 mg, 93% yield). 1H NMR (400 MHz, Methanol-D4) δ (ppm): 8.05 (d, J=8.2 Hz, 1H), 7.82 (d, J=8.2 Hz, 1H), 4.47 (m, 1H), 3.87 (t, J=11.8, 11.8 Hz, 1H), 3.38 (m, 4H), 2.39 (m, 1H), 2.27 (m, 2H), 2.13 (t, J=8.2 Hz, 1H). LCMS (ESI): m/z 299.1 (M+H [C15H17F3N2O]=299.13).

Workup

  1. customwas subsequently injected into a Preparative HPLC instrument for purification
  2. concentrationconcentrated under vacuum
  3. customrecrystallized from 4 mL of Methanol/water (3:2)

Sources & evidence

ORD record
ord-e8e5516bddd942bda5e7a0117c9df3d4
Source dataset
uspto-grants-2013_05
Patent number
US08435762B2

Reaction notes

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