Sodium Carbonate → (6-Methylsulfonyl-indan-2-yl)-dipropyl-amine

Reaction equation

CSC1C=[C:10]2C(C[CH:8]([N:12]([CH2:16][CH2:17]C)[CH2:13][CH2:14][CH3:15])[CH2:9]2)=CC=1.Cl[C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23](OO)=O.C([O-])([O-])=O.[Na+].[Na+].F[C:37](F)(F)[S:38](O)(=[O:40])=[O:39]>>[CH3:37][S:38]([C:29]1[CH:28]=[C:27]2[C:22]([CH2:23][CH:16]([N:12]([CH2:8][CH2:9][CH3:10])[CH2:13][CH2:14][CH3:15])[CH2:17]2)=[CH:21][CH:20]=1)(=[O:40])=[O:39]

Participants

Reactant 4

HCID 10340Sodium Carbonate

HCID 62406Trifluoromethanesulfonic acid

HCID 70297m-Chloroperbenzoic acid2×

HCID 19710198(6-Methylsulfanyl-indan-2-yl)-dipropyl-amine

Product 1

HCID 19710185(6-Methylsulfonyl-indan-2-yl)-dipropyl-amineYield 69%

Procedure

To a solution of (6-methylsulfanyl-indan-2-yl)-dipropyl-amine (Example 12, 85 mg, 0.32 mmol) in trifluoromethanesulfonic acid (5 ml) was added 3-chloroperoxy-benzoic acid (90 mg, 75%, 0.39 mmol). The solution was then stirred for 2 h at room temperature. Another portion of 3-chloroperoxy-benzoic acid (20 mg 75%, 0.09 mmol) was added and the reaction mixture was stirred for an additional 1 h. The pH was adjusted to 11 with aqueous Na2CO3 and the layers were separated. The organic layer was dried and evaporated to dryness. The crude product was chromatographed (SiO2) using dichloromethane-methanol as eluant (19:1). Pooling of the pure fractions yielded 65 mg (69%) of (6-methylsulfonyl-indan-2-yl)-dipropyl-amine. The amine was converted to the hydrochloride and recrystallized from a mixture of 2-propanol and isopropyl ether. m.p. 190-192 (HCl); 1H NMR (300 MHz, CDCl3) δ 0.90 (t, 6H), 1.50 (m, 4H), 2.50 (t, 4H), 2.90-3.20 (m, 7H), 3.70-3.80 (m, 1H), 7.40 (d, J=8 Hz, 1H), 7.70-7.80 (d, 2H); 13C NMR (75.4 MHz, CDCl3) δ 11.97, 20.25, 36.43, 36.82, 44.68, 53.29, 63.08, 123.33, 125.18, 125.81, 138.65, 143.72, 148.89; MS m/e 295 (5, M+), 266 (100), 116 (18), 267 (18), 115 (15).