Acetic Acid → HCID 12052522, 화합물

반응식

[CH3:1][N:2]1[C@H:14]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:9]=[CH:10][N:11]=[CH:12][C:13]=32)[CH2:4][CH2:3]1.[I:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[CH3:27]C(O)=O>>[I-:15].[CH2:26]([N+:11]1[CH:10]=[CH:9][C:8]2[CH2:7][CH2:6][C@@H:5]3[CH2:4][CH2:3][N:2]([CH3:1])[C@@H:14]3[C:13]=2[CH:12]=1)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:27]

참가 물질

반응물 3

HCID 176Acetic Acid

HCID 20276Undecane, 1-iodo-

HCID 6336060HCID 6336060, 화합물

생성물 1

HCID 12052522HCID 12052522, 화합물수율 66%

실험 절차

To a stirred solution of cis-1-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-h]isoquinoline (120 mg, 0.64 mmol) in AcOH (2 ml) was added 1-iodoundecane (569 mg, 1.92 mmol). The mixture was heated at reflux under nitrogen for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3. The mixture was washed with saturated aqueous NaHCO3, water and brine successively and dried. Evaporation of the solvent followed by titration with ether afforded 205 mg (66%) of cis-8-dodecyl-1-methyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-h]isoquinolin-8-ium iodide (ACDD) as a brown oil. 1H NMR (300 MHz, CDCl3) δ9.08 (1H, s, C9-H), 9.02 (1H, d, J6.3 Hz, C7-H), 7.79 (1H, d, J6.3 Hz, C6-H), 4.90 (2H, m. pyCH2), 3.48 (1H, d, J8.4 Hz, C9b-H), 2.36 (3H, s, NCH3), 1.50-3.10 (9H, m, CH2+CH), 2.00 (2H, m, pyCH2CH2), 1.10-1.40 (18H, m, 9×CH2), 0.85 (3H, t, J6.9 Hz, CH2CH3); 13C NMR (75 MHz, CDCl3) δ161.5, 143.3, 142.5, 138.8, 127.5, 63.1, 61.0, 55.7, 41.0, 35.6, 32.0, 31.9, 30.0, 29.6×2, 29.5, 29.4, 29.3, 29.1, 28.1, 27.3, 26.0, 22.7, 14.1.