Triethylamine → HCID 45381301, compound

HRID 2088312Notes

Reaction equation

HRID 2088312 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.[CH2:19]([C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=1)[CH2:20][CH2:21][CH3:22].[I-].ClC1C=CC=C[N+]=1C>O.C(#N)C>[CH2:19]([C:23]1[CH:24]=[CH:25][C:26]([C:27]([NH:10][C@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:28])=[CH:30][CH:31]=1)[CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 886314-Butylbenzoic acidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride

Product 1

HCID 45381301HCID 45381301, compoundYield 95%

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 4-Butylbenzoic acid (196 mg, 1.1 mmol), followed by addition of 2-Chloro-1-methylpyridinium 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)-4-butyl-N-(quinuclidin-3-yl)benzamide (272 mg, 95% yield) was isolated as an oil. 1H NMR (400 MHz, Methanol-D4) δ (ppm): 8.24 (d, J=8.2 Hz, 2H), 8.41 (d, J=8.4 Hz, 2H), 4.42 (m, 1H), 3.84 (ddd, J=11.7, 9.9, 2.6 Hz, 1H), 3.35 (m, 4H), 2.69 (t, J=7.7 Hz, 2H), 2.36 (q, J=3.1 Hz, 1H), 2.24 (m, 1H), 2.10 (m, 2H), 1.94 (m, 1H), 1.62 (q, J=7.6 Hz, 2H), 1.37 (q, J=7.4 Hz, 2H), 0.95 (t, J=7.4 Hz, 3H). LCMS (ESI): m/z 287.1 (M+H [C18H26N2O]=287.20).

Workup

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

Sources & evidence

ORD record
ord-0cd0b1b350fb47a2806158a560d6c324
Source dataset
uspto-grants-2013_05
Patent number
US08435762B2

Reaction notes

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