4-Iodoaniline → HCID 21072621, compound

HRID 1372868Notes

Reaction equation

HRID 1372868 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=O)[CH2:3]2.[I:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[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+]>CC(O)=O>[I:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][CH:4]2[CH:5]3[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]3)[CH2:3]2)=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 108934-IodoanilineHCID 24436Sodium SulfateHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21072621HCID 21072621, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Quinuclidinone hydrochloride (Aldrich, 3.22 g, 20 mmol) was treated with 4-iodo-aniline (Aldrich, 2.19 g, 10 mmol), Na2SO4 (anhydrous, Aldrich, 7.40 g, 50 mmol) and NaBH(OAc)3 (Aldrich, 3.16 g, 15 mmol) in HOAc (25 mL) at ambient temperature for 15 h. After the reaction was complete, the reaction mixture was slowly poured into a flask containing 75 mL of saturated NaHCO3 and stirred for 20 min. It was then extracted with EtOAc (3×100 mL). The extracts were combined and washed with brine (2×20 mL). The organic solution 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 oil (3.24 g, yield, 98%). 1H NMR (300 MHz, CD3OD,) δ 1.70–1.81 (m, 1H), 1.93–2.04 (m, 2H), 2.08–2.24 (m, 2H), 2.89 (ddd, J=12.9, 5.1, 2.7 Hz, 1H), 3.12–3.28 (m, 4H), 3.64 (ddd, J=12.9, 9.5, 2.4 Hz, 1H), 3.79–3.85 (m, 1H), 6.46 (dt, J=9.0, 2.7 Hz, 2H), 7.39 (dt, J=9.1, 2.7 Hz, 2H) ppm. MS (DCl/NH3) m/z 329 (M+H)+.

Workup

  1. additionthe reaction mixture was slowly poured into a flask
  2. extractionIt was then extracted with EtOAc (3×100 mL)
  3. washwashed with brine (2×20 mL)
  4. concentrationThe organic solution 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 oil (3.24 g, yield, 98%)

Sources & evidence

ORD record
ord-cc86a32785e948cab45871019e0495cf
Source dataset
uspto-grants-2007_01
Patent number
US07160876B2

Reaction notes

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