Morpholine → HCID 10476225, compound

HRID 2164670Notes

Reaction equation

HRID 2164670 reaction equation
[CH:1]([NH:4][CH2:5][CH:6]1[CH2:10][O:9][C:8]2([CH:18](Br)[CH2:17][CH2:16][C:15]3[N:14]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH:13]=[CH:12][C:11]2=3)[O:7]1)([CH3:3])[CH3:2].N1CCOCC1>>[CH:1]([NH:4][CH2:5][CH:6]([OH:7])[CH2:10][O:9][C:8]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][N:14]2[S:20]([C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 12946401HCID 12946401, compound

Product 1

HCID 10476225HCID 10476225, compoundYield 29%

Procedure

In a flask equipped with a reflux condenser is placed 4'-isopropylaminomethyl-5-bromo-1-p-toluenesulfonyl-4,5,6,7-tetrahydroindole-4-spiro-2'-[1,3]dioxolane (100 parts) and morpholine. The solution is refluxed for 20 hours. After cooling, the reaction mixture is concentrated in vacuo to leave resin. Chromatographic purification of the resin affords 4-(3-isopropylamino-2-hydroxypropoxy)-1-p-toluenesulfonylindole (24 parts) in 29% yield. This showed the same physical characteristics with an authentic sample.

Workup

  1. customIn a flask equipped with a reflux condenser
  2. temperatureThe solution is refluxed for 20 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture is concentrated in vacuo
  5. customto leave resin
  6. customChromatographic purification of the resin

Sources & evidence

ORD record
ord-9156bc2309764fe99e0963a1b519e33b
Source dataset
uspto-grants-1985_03
Patent number
US04506079

Reaction notes

Loading…