4-(4-Chlorophenoxy)aniline → HCID 69521078, compound

HRID 1294686Notes

Reaction equation

HRID 1294686 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=O)[CH2:3]2.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1.O1CCOCC1.Cl>C(OCC)(=O)C>[ClH:11].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:25]=[CH:24][C:22]([NH:23][CH:4]3[CH:5]4[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]4)[CH2:3]3)=[CH:21][CH:20]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 75784-(4-Chlorophenoxy)anilineHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)HCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 69521078HCID 69521078, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Quinuclidinone hydrochloride (Aldrich, 1.61 g, 10 mmol) was treated with 4-(4-chlorophenyloxy) aniline (Aldrich, 1.10 g, 5.0 mmol) according to the procedure of Example 30A. The free base of the title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.10) as a solid (1.52 g, yield, 93%). MS (DCl/NH3) m/z 329 (M+H)+, 331 (M+H)+. The free base (200 mg, 0.61 mmol) was treated with 4M HCl 1,4-dioxane (0.5 mL, 2.0 mmol) in ethyl acetate (5 mL). The hydrochloride salt of the title compound was obtained as a solid (195 mg, yield, 80%). 1H NMR (MeOH-d4, 300 MHz) δ 1.90–2.18 (m, 3H), 2.35–2.45 (m, 2H), 3.24 (ddd, J=12.5, 5.4, 2.3 Hz, 1H) 3.30–3.50 (m, 4H), 3.82 (ddd, J=12.2, 9.8, 2.7 Hz, 1H), 3.95–4.10 (m, 1H), 6.91 (dt, J=9.1, 2.3 Hz, 2H), 6.95–7.02 (m, 4H), 7.30(dt, J=9.2, 2.4 Hz, 1H), 7.26–7.32 (m, 2H) ppm. MS (DCl/NH3) m/z 329 (M+H)+, 331 (M+H)+. Anal Calculated for C19H21ClN2O.2.0HCl.0.5H2O: C, 55.56; H, 5.89; N, 6.82. Found: C, 55.78; H, 5.28; N, 6.62.

Workup

  1. customThe free base of the title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.10) as a solid (1.52 g, yield, 93%)

Sources & evidence

ORD record
ord-d6eb4f98df9f44ca9688364c99ce4d96
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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