(4-Aminophenoxy)benzene → HCID 11254890, compound

HRID 1294684Notes

Reaction equation

HRID 1294684 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=O)[CH2:3]2.[O:11]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(O)(=O)C>[O:11]([C:18]1[CH:19]=[CH:20][C:21]([NH:22][CH:4]2[CH:5]3[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]3)[CH2:3]2)=[CH:23][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 8764(4-Aminophenoxy)benzeneHCID 24436Sodium SulfateHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 11254890HCID 11254890, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Quinuclidinone hydrochloride (Aldrich, 1.61 g, 10 mmol) in acetic acid (25 mL) was treated with 4-phenoxyaniline (Aldrich, 0.93 g, 5.0 mmol), Na2SO4 (anhydrous, Aldrich, 7.40 g, 50 mmol) and NaBH(OAc)3 (Aldrich, 3.16 g, 15 mmol) at ambient temperature for 15 hours. The reaction mixture was slowly poured into a flask containing 75 mL of saturated NaHCO3, stirred for 20 minutes, and extracted with ethyl acetate (3×100 mL). The extracts were combined and washed with brine (2×20 mL). The organic phase was concentrated under reduced pressure and the title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.10) as a solid (1.46 g, yield, 99%). 1H NMR (MeOH-d4, 300 MHz) δ 1.78–1.90 (m, 1H), 2.00–2.10 (m, 2H), 2.22–2.35 (m, 2H), 3.05 (ddd, J=12.9, 4.7, 2.0 Hz, 1H) 3.20–3.40 (m, 4H), 3.78 (ddd, J=12.9, 9.5, 2.4 Hz, 1H), 3.90–3.98 (m, 1H), 6.65–6.75 (m, 2H), 6.80–6.90 (m, 4H), 6.99 (tt, J=7.5, 1.0 Hz, 1H), 7.20–7.29 (m, 2H) ppm. MS (DCl/NH3) m/z 295 (M+H)+.

Workup

  1. additionThe reaction mixture was slowly poured into a flask
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washwashed with brine (2×20 mL)
  4. concentrationThe organic phase was concentrated under reduced pressure
  5. customthe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.10) as a solid (1.46 g, yield, 99%)

Sources & evidence

ORD record
ord-a990f367d8b24821bb7ec59831f834fd
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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