1H-indole-3-propylamine → 2-{[3-(Indol-3-yl)-propylamino]-methyl}-2,3,8,9-tetrahydro-7H-1,4-dioxino-[2,3-e]indol-8-one

HRID 1292192

Reaction equation

HRID 1292192 reaction equation
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[O:25][C:16]3=[C:17]4[C:21](=[CH:22][CH:23]=[C:15]3[O:14][CH2:13]2)[NH:20][C:19](=[O:24])[CH2:18]4)(=O)=O)=CC=1.[NH2:27][CH2:28][CH2:29][CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1>CS(C)=O>[NH:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:31]([CH2:30][CH2:29][CH2:28][NH:27][CH2:11][CH:12]2[O:25][C:16]3=[C:17]4[C:21](=[CH:22][CH:23]=[C:15]3[O:14][CH2:13]2)[NH:20][C:19](=[O:24])[CH2:18]4)=[CH:32]1

Participants

4

Reactant 2

HCID 289891H-indole-3-propylamineHCID 15381104(R)-2-(Toluene-4-sulfonyloxymethyl)-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-one

Product 1

HCID 104072412-{[3-(Indol-3-yl)-propylamino]-methyl}-2,3,8,9-tetrahydro-7H-1,4-dioxino-[2,3-e]indol-8-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
75 °C

Procedure

(R)-2-(Toluene-4-sulfonyloxymethyl)-2,3,8,9-tetrahydro-7H-1,4-dioxino-[2,3-e]indol-8-one (1.5 g, 4.2 mmole) in DMSO (80 ml) was slowly added through a dropping funnel to 3-(3-aminopropyl)indole (1.1 g, 6.3 mmole) in DMSO (50 ml) and the mixture was heated at 75° C. for 17 hours. Most of DMSO was removed under reduced pressure and the residue was then partitioned between water and dichloromethane/isopropanol (3/1) solution. The separated organic layer was dried over anhydrous sodium sulfate, filtered, concentrated in vacuum and column chromatographed on silica gel using first ethyl acetate/hexane (7/3), then ethyl acetate and finally 5% methanol in ethyl acetate as eluants. The expected product was isolated, treated with 0.25M ethanolic fumaric acid and precipitated with a minimum amount of hexane to give 70 mg of the (S) enantiomer of the title compound as a tan solid fumarate salt, Mass spec (m/e), 377 (M+).

Workup

  1. customMost of DMSO was removed under reduced pressure
  2. customthe residue was then partitioned between water and dichloromethane/isopropanol (3/1) solution
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum and column
  6. customchromatographed on silica gel using first ethyl acetate/hexane (7/3)

Sources & evidence

ORD record
ord-3d5e28a242a14e2d9229a4e4e4b8df45
Source dataset
uspto-grants-1998_05
Patent number
US05756532

Linked notes

Loading…