Butylamine → (4-Benzylpiperidin-1-yl)-(2-propyl-8H-oxazolo[5,4-g]indol-7-yl)methanone

HRID 902141Notes

Reaction equation

HRID 902141 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[NH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[C:20]([OH:25])[CH:19]=3)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([NH2:30])[CH2:27][CH2:28][CH3:29].COCCOC>[O-2].[O-2].[Mn+4]>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([C:14]([C:16]2[NH:17][C:18]3[C:19]4[N:30]=[C:26]([CH2:27][CH2:28][CH3:29])[O:25][C:20]=4[CH:21]=[CH:22][C:23]=3[CH:24]=2)=[O:15])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8007ButylamineHCID 80711,2-DimethoxyethaneHCID 9797767(4-benzylpiperidin-1-yl)-(6-hydroxy-1H-indol-2-yl)methanone

Product 1

HCID 22350188(4-Benzylpiperidin-1-yl)-(2-propyl-8H-oxazolo[5,4-g]indol-7-yl)methanoneYield 124.5%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

Under argon, to a solution of 0.5 g (1.49 mmol) of 1-(4-benzylpiperidine-1-yl)-1-(6-hydroxy-1H-indole-2-yl)methanone and 0.14 g (0.2 mmol) of n-butylamine in 100 ml of ethylene glycol dimethyl ether 10 g (115 mmol) of manganese dioxide is added portion-wise at 0° C. After stirring for 1 h, the reaction mixture is filtered, the filtrate is concentrated and the residue is purified by column chromatography using Kieselgel 60 as adsorbent (Merck) and hexane:ethyl acetate=2:1 as eluent to yield 0.1 g (17.3%) of the title compound. Mp.: 195-196° C. (hexane-ethyl acetate).

Workup

  1. filtrationthe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-c0e8a55706e94bdb88cbce5823505872
Source dataset
uspto-grants-2008_04
Patent number
US07365083B2

Reaction notes

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