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Saturday 6 September 2014

1-((3-Methoxyphenyl)sulfonyl)piperidine: Piperidine, 1-[(3-methoxyphenyl)sulfonyl]-

Reaction scheme

compd 1
3-Methoxy-N-morpholinobenzenesulfonamide: Benzenesulfonamide, 3-methoxy-N-4-morpholinyl-; (1) (1255365-27-5)

1H NMR pdf(400 MHz, CDCl3, 7.27 ppm) δ: 2.64 (t, J = 4.8 Hz, 4 H (NCH2CH2O)2), 3.62 (t, J = 4.8 Hz, 4 H, (NCH2CH2O)2), 3.87 (s, 3 H, OMe), 5.60 (s, 1 H, NH), 7.14 (dd, = 8.0, 2.0 Hz, 1 H, Ar-H), 7.43 (t, = 8.0 Hz, 1 H, Ar-H), 7.49 (t, J = 2.0 Hz, 1 H, Ar-H), 7.57 (d,J = 8.0 Hz, 1 H, Ar-H); 13C NMR pdf(100 MHz, CDCl3, 77.0 ppm) δ: 55.6, 56.4, 66.5, 112.5, 119.4, 120.1, 129.8, 139.7, 159.6; IR n max (film)/cm-1 3212, 2963, 2856, 1597, 1478, 1433, 1361, 1317, 1287, 1242, 1157, 1109, 1034, 864, 685 (principal peaks); HRMS (FTMS+ p-NSI) found m/z 295.0721 [M+Na]+, C11H16N2O4SNa requires m/z 295.0723. Reverse phase HPLC analysis reveals purity >99% (run on an Agilent Zorbax SB-C18, 5 µm, 4.6 x 150 mm column (23 °C) at a flow rate of 1.5 mL/min of 70:30 MeCN:H2O observed at 210 nm giving a retention time of 1.32 min, 1.0 mg/mL in CH3CN).


compd 2

1-((3-Methoxyphenyl)sulfonyl)piperidine: Piperidine, 1-[(3-methoxyphenyl)sulfonyl]-; (2) (173681-65-7)
mp 115-116 °C;


 1H NMR pdf(400 MHz, DMSO-d6, 2.50 ppm) 
δ: 1.30-1.35 (m, 2 H, N(CH2CH2)2CH2), 
1.47-1.52 (m, 4 H, N(CH2CH2)2CH2),
2.85 (t, J = 5.2 Hz, 4 H, N(CH2CH2)2CH2), 
3.83 (s, 3 H, OMe), 
7.16 (t, J = 2.1 Hz, 1 H, Ar-H), 
7.25-7.30 (m, 2 H, Ar-H), 
7.55 (t, J = 8.0 Hz, 1 H, Ar-H);





 13C NMRpdf(100 MHz, DMSO-d6, 39.5 ppm) δ: 22.8, 24.7, 46.6, 55.6, 112.3, 118.7, 119.5, 130.5, 136.7, 159.5; 


IR nmax(film)/cm-1 2940, 2851, 1597, 1478, 1359, 1340, 1318, 1287, 1241, 1167, 1098, 1040, 931, 856, 724, 688; (principal peaks); 


HRMS (FTMS+p-NSF) found m/z 256.1002 [M+H]+, C12H18 NO3S requires m/z 256.1002. 

Reverse phase HPLC analysis reveals purity >99% (run on an Agilent Zorbax SB-C18, 5 µm, 4.6 x 150 mm column (23 °C) at a flow rate of 1.5 mL/min of 75:25 MeCN:H2O observed at 210 nm giving a retention time of 1.95 min, 1.0 mg/mL in MeCN).




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