Dimethylformamide → HCID 131726123, compound

HRID 1917050Notes

Reaction equation

HRID 1917050 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:12]([N:13]=[C:14]=[O:15])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.Cl.[N:17]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[C@@H:19](O)[CH2:18]2.CN(C)C=[O:29]>C(OCC)(=O)C>[N:17]12[CH2:18][CH:19]([CH2:21][CH2:22]1)[C@H:20]([O:15][C:14](=[O:29])[NH:13][C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[CH2:23][CH2:24]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2222801-Isocyanato-2-phenylbenzeneHCID 16216954(3R)-1-Azabicyclo[2.2.2]octan-3-ol--hydrogen chloride (1/1)

Product 1

HCID 131726123HCID 131726123, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Biphenyl isocyanate (1.00 g, 5.12 mmol) and (R)-(−)-3-quinuclidinol hydrochloride (921 mg, 5.63 mmol) were heated together in N,N-dimethylformamide (2.06 mL) at 110° C. for 12 h. The reaction mixture was cooled and diluted with ethyl acetate (15 mL) and then washed with saturated aqueous sodium bicarbonate (2×10 mL). The organic layer was extracted with 1 M hydrochloric acid (3×20 mL) and the combined aqueous extracts were made basic to pH 8-9 with potassium carbonate. The aqueous layer was then extracted with ethyl acetate (3×20 mL) and the combined organic layers were dried (magnesium sulfate) and solvent was removed under reduced pressure to give the title compound as a yellow oil (1.64 g, 99% yield).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with saturated aqueous sodium bicarbonate (2×10 mL)
  3. extractionThe organic layer was extracted with 1 M hydrochloric acid (3×20 mL)
  4. extractionThe aqueous layer was then extracted with ethyl acetate (3×20 mL)
  5. dry with materialthe combined organic layers were dried (magnesium sulfate) and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-aa9c9cba1384416e90a776f7040a0c11
Source dataset
uspto-grants-2013_12
Patent number
US08618131B2

Reaction notes

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