Hydrochloric Acid → (S)-3-(4-phenoxyphenoxy)quinuclidine hydrochloride

HRID 1294647

Reaction equation

HRID 1294647 reaction equation
[O:1]([C:8]1[CH:22]=[CH:21][C:11]([O:12][C@H:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:23]>C(OCC)(=O)C.O1CCOCC1>[ClH:23].[O:1]([C:8]1[CH:22]=[CH:21][C:11]([O:12][C@H:13]2[CH:18]3[CH2:17][CH2:16][N:15]([CH2:20][CH2:19]3)[CH2:14]2)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11392280(S)-3-(4-phenoxyphenoxy)quinuclidine

Product 1

HCID 69520862(S)-3-(4-phenoxyphenoxy)quinuclidine hydrochlorideYield 63%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

The product of Example 4A (80 mg, 0.27 mmol) in ethyl acetate (4 mL) was treated with 4M HCl in 1,4-dioxane (0.5 mL) to provide the title compound as solid (57 mg, yield, 63%). 1H NMR (MeOH-d4, 300 MHz) δ 1.80–2.20 (m, 3H), 2.30–2.40 (m, 1H), 2.50 (m, 1H), 3.30–3.45 (m, 5H), 3.76 (m, 1H), 4.90 (m, 1H), 6.90–6H), 7.05–7.09 (m, 1H) 7.20–7.42 (m, 2H) ppm. MS (DCl/NH3) m/z 296(M+H)+. A calculated for C19H21NO2. 1.0HCl: C, 68.77; H, 6.68; N, 4.22. Found: C, 68.50; H, 6.69; N, 4.12.

Sources & evidence

ORD record
ord-6b72017097b8467d8555c52d2046cb27
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Linked notes

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