Potassium Carbonate → N-[2-(1-Piperidyl)ethyl] 3,4-dihydro-2 H-[1,3]oxazino[3,2-a]indole-10-Carboxamide

HRID 609592Notes

Reaction equation

HRID 609592 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClN1[C:26](=[O:27])[CH2:25][CH2:24]C1=O.BrCCCO.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]3[CH2:24][CH2:25][CH2:26][O:27][C:13]=23)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 31398ChlorosuccinimideHCID 10635843N-[2-(1-Piperidyl)ethyl] 1H-indole-3-carboxamide

Product 1

HCID 19599429N-[2-(1-Piperidyl)ethyl] 3,4-dihydro-2 H-[1,3]oxazino[3,2-a]indole-10-CarboxamideYield 29%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-[2-(1-Piperidyl)ethyl] 1H-indole-3-carboxamide (D2) was treated initially with N-chlorosuccinimide then with 3-bromo-1-propanol, then with potassium carbonate in acetone following the method described in Example 3. The crude product was chromatographed on silica gel eluting with chloroform/methanol (19:1) to give a pale yellow oil, which crystallised from ether to afford the title compound (E5) as a white solid (29%) mp 124-127° C.

Workup

  1. customThe crude product was chromatographed on silica gel eluting with chloroform/methanol (19:1)
  2. customto give a pale yellow oil, which
  3. customcrystallised from ether

Sources & evidence

ORD record
ord-fb2912d5b10c406b8a3bdf8c98ab458e
Source dataset
uspto-grants-1999_12
Patent number
US05998409

Reaction notes

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