(R)-(+)-3-Chlorostyrene oxide → 3-{(2 R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carboxylic acid diethylamide

HRID 1351936Notes

Reaction equation

HRID 1351936 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C@H:16]([NH2:18])[CH3:17])=[O:5])[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C@H:25]1[O:27][CH2:26]1>C(#N)C>[CH2:19]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C@H:16]([NH:18][CH2:26][C@@H:25]([C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([Cl:21])[CH:23]=1)[OH:27])[CH3:17])=[O:5])[CH3:20]

Participants

4

Reactant 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 69457261(R)-3-(2-aminopropyl)-1H-indole-7-carboxylic acid diethylamide

Product 1

HCID 694562293-{(2 R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carboxylic acid diethylamideYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)-3-(2-aminopropyl)-1H-indole-7-carboxylic acid diethylamide (1.30 g, 4.76 mmol) and (R)-(+)-3-chlorostyrene oxide (1.21 mL, 9.52 mmol) in acetonitrile (15 mL) is refluxed for 10 hours. After cooling, the mixture is concentrated and the residue is purified by silica gel column chromatography (a saturated ammonia solution in chloroform) to give the desired 3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carboxylic acid diethylamide (0.79 g, yield: 39%).

Workup

  1. temperatureis refluxed for 10 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. customthe residue is purified by silica gel column chromatography (a saturated ammonia solution in chloroform)

Sources & evidence

ORD record
ord-6f6f286a711e44f0a28666cc9f324937
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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