Lipoic acid → N-[3-[3-[1-(Dimethylamino)ethyl]phenoxy]propyl]-1,2-dithiolane-3-pentanamide

HRID 969291Notes

Reaction equation

HRID 969291 reaction equation
[CH3:1][N:2]([CH3:16])[CH:3]([C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[O:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH3:4].[CH2:17]1[C@@H:21]([CH2:22][CH2:23][CH2:24][CH2:25][C:26](O)=[O:27])[S:20][S:19][CH2:18]1>>[CH3:16][N:2]([CH3:1])[CH:3]([C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[O:8][CH2:9][CH2:10][CH2:11][NH:12][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[CH2:17][CH2:18][S:19][S:20]1)[CH3:4]

Participants

3

Reactant 2

HCID 6112Lipoic acidHCID 56930628HCID 56930628, compound

Product 1

HCID 11647230N-[3-[3-[1-(Dimethylamino)ethyl]phenoxy]propyl]-1,2-dithiolane-3-pentanamide

Procedure

5-[1,2]dithiolan-3-yl-pentanoic acid {3-[3-(1-dimethylamino-ethyl)-phenoxy]-propyl}-amide (19) was synthesized from 19c (150 mg, 0.67 mmol) and lipoic acid (210 mg, 1.02 mmol) following the procedure described for 17, and purified by gravity column. Elution with petroleum ether/toluene/CH2Cl2/MeOH/aqueous 30% ammonia solution (6:1:1.5:1.5:0.01) afforded 19 as a waxy solid; 30% yield, 1H NMR (200 MHz, CDCl3) δ 7.27 (t, J=8.2 Hz, 1H); 6.78-6.98 (m, 3H), 5.99 (br t, 1H); 4.09 (t, J=6.0 Hz, 2H); 3.21-3.62 (m, 5H), 3.05-3.19 (m, 3H), 2.40-2.53 (m, 1H), 2.32 (s, 6H), 2.22 (t, J=7.2 Hz, 2H); 1.81-2.0 (m, 3H), 1.65-1.73 (m, 4H), 1.47 (d, J=6.6 Hz, 3H); MS (ESI+) m/z 411 (M+H)+. Anal. Calculated for C21H34N2O2S2: C, 61.42; H, 8.35; N, 6.82. Found: C, 61.62; H, 8.36, N, 6.80.

Workup

  1. custompurified by gravity column
  2. washElution with petroleum ether/toluene/CH2Cl2/MeOH/aqueous 30% ammonia solution (6:1:1.5:1.5:0.01)

Sources & evidence

ORD record
ord-580f0678d8d049afb6a0bd8bd44a62e0
Source dataset
uspto-grants-2007_12
Patent number
US07307083B2

Reaction notes

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