Sodium Hydroxide → HCID 59331187, compound

HRID 2088322Notes

Reaction equation

HRID 2088322 reaction equation
CCN(C(C)C)C(C)C.Cl.Cl.[NH2:12][C@H:13]1[CH:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH2:14]1.[I:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.[OH-].[Na+]>CN(C=O)C>[I:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:12][C@H:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[O:27])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 743734-Iodobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride

Product 1

HCID 59331187HCID 59331187, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N′-Diisopropylethylamine (1.05 ml, 6.03 mmol) was added to a flask charged with DMF solution mixture of (S)-(−)-3-Aminoquinuclidine dihydrochloride (400 mg, 2.01 mmol) and 4-Iodobenzoyl chloride (616 mg, 2.31 mmol). The clear yellow solution was stirred for 3 hours. The reaction mixture was worked up by addition of 1N sodium hydroxide aqueous solution and extracted twice with ethyl acetate, combined organic layer was washed with saturated brine solution, dried over sodium sulfate, filtered, and concentrated to crude clear oil. The crude oil was purified via preparative HPLC to obtain pure product of (S)-4-iodo-N-(quinuclidin-3-yl)benzamide, (460 mg, 64% yield). 1H NMR (400 MHz, Methanol-D4) δ (ppm): 7.85 (d, J=8 Hz, 2H), 7.60 (d, J=8 Hz, 2H), 4.12 (m, 1H), 3.31 (m, 1H), 2.99 (m, 1H), 2.84 (m, 4H), 2.02 (m, 1H), 1.90 (m, 1H), 1.78 (m, 2H), 1.54 (m, 1H). C14H17IN2O=356.04 LCMS (M+H): m/z 357

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwas washed with saturated brine solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to crude clear oil
  6. customThe crude oil was purified via preparative HPLC

Sources & evidence

ORD record
ord-84da32e7f652409fb03d04d1fba25ace
Source dataset
uspto-grants-2013_05
Patent number
US08435762B2

Reaction notes

Loading…