4-(p-Tolyloxy)aniline → HCID 11324300, compound

HRID 1294687Notes

Reaction equation

HRID 1294687 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=O)[CH2:3]2.[CH3:11][C:12]1[CH:25]=[CH:24][C:15]([O:16][C:17]2[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=2)=[CH:14][CH:13]=1>>[CH3:11][C:12]1[CH:25]=[CH:24][C:15]([O:16][C:17]2[CH:23]=[CH:22][C:20]([NH:21][CH:4]3[CH:5]4[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]4)[CH2:3]3)=[CH:19][CH:18]=2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 945194-(p-Tolyloxy)anilineHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)

Product 1

HCID 11324300HCID 11324300, compound

Procedure

3-Quinuclidinone hydrochloride (Aldrich, 1.61 g, 10 mmol) was treated with 4-(4-methylphenoxy)aniline (0.99 g, 5.0 mmol) according to the procedure of Example 30A. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.10) as an oil (1.48 g, yield, 95%). 1H NMR (MeOH-d4, 300 MHz) δ 1.55–1.70 (m, 1H), 1.78–1.95 (m, 2H), 2.00–2.15 (m, 2H), 2.28 (s, 3H), 2.71 (ddd, J=12.9, 5.1, 2.2 Hz, 1H), 2.95–3.10 (m, 4H), 3.46 (ddd, J=12.9, 9.5, 2.4 Hz, 1H), 3.60–3.70 (m, 1H), 6.64 (dt, J=9.0, 2.7 Hz, 2H), 6.72–6.84 (m, 4H), 7.06 (dt, J=9.1, 2.8 Hz, 2H) ppm. MS (DCl/NH3) m/z 309 (M+H)+.

Workup

  1. customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.10) as an oil (1.48 g, yield, 95%)

Sources & evidence

ORD record
ord-0ba80db90b0a4ddbba605350cb7483b2
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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