Triethylamine → 6-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-1-methyl-6-aza-3-azoniaspiro[2.5]octane chloride
Reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH:17]([CH3:20])[CH2:18]O)[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.S([Cl:32])(C)(=O)=O>C(Cl)Cl>[Cl-:32].[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][N+:14]4([CH:17]([CH3:20])[CH2:18]4)[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
Crude compound IV (29.4 g, 0.106 mol), and triethyl amine (16.2 mL, 0.116 mol) are dissolved in CH2Cl2 (150 mL) and to this solution is added a solution of mesyl chloride (8.6 mL, 0.111 mol) in CH2Cl2 (50 mL) under cooling at 5 to 15° C. over 0.5 h. Stirring is continued overnight at ambient temperature resulting in clear red solution. This solution is washed with water (1×100 mL) and 5% aq. NaHCO3 (1×100 mL). Combined aqueous layers were back-washed with CH2Cl2 (2×50 mL). Organic layers are dried with MgSO4 and concentrated to afford V as thick red oil, yield 31.6 g (101%). 1H NMR (CDCl3) δ 6.76 (t, J=7.5 Hz, 1H), 6.55 (m, 2H), 4.27 (m, 4H), 4.11 (m, 1H), 3.10 (m, 4H), 2.8–2.64 (m, 5H), 2.54 (dd, J=7.5, 15 Hz, 1H), 1.55 (d, 3H).
Workup
- customresulting in clear red solution
- washThis solution is washed with water (1×100 mL) and 5% aq. NaHCO3 (1×100 mL)
- washCombined aqueous layers were back-washed with CH2Cl2 (2×50 mL)
- dry with materialOrganic layers are dried with MgSO4
- concentrationconcentrated
- customto afford V as thick red oil, yield 31.6 g (101%)
Sources & evidence
- ORD record
- ord-b76a6354ffcf4de38c61a0fa061d1f6a
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091349B2
Reaction notes
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