Triethylamine → N-[(1-(3-Phenoxypropyl)-4-piperidinyl)methyl]3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide

HRID 1458615

Reaktionsgleichung

Reaktionsgleichung von HRID 1458615
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]3[CH2:20][CH2:21][CH2:22][O:23][C:12]=23)=[O:10])[CH2:3][CH2:2]1.C(N(CC)CC)C.[O:31]([CH2:38][CH2:39][CH2:40]Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(#N)C.CN(C)C=O>[O:31]([CH2:38][CH2:39][CH2:40][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]3[CH2:20][CH2:21][CH2:22][O:23][C:12]=23)=[O:10])[CH2:3][CH2:2]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 68522Benzene, (3-bromopropoxy)-HCID 9839803N-(4-Piperidylmethyl) 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide

Produkt 1

HCID 9868253N-[(1-(3-Phenoxypropyl)-4-piperidinyl)methyl]3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A stirred solution of N-(4-piperidinylmethyl) 3,4-dihydro-2 H-[1,3]oxazino[3,2-a]indole-10-carboxamide (E21) (250 mg, 0.80 mmole) and triethylamine (0.25 ml, 1.8 mmole) in a mixture of acetonitrile (15 ml) and N,N-dimethylformamide (10 ml) was treated with 3-phenoxypropyl bromide (0.13 ml, 0.88 mmole) and the solution heated under reflux for 48 h. The mixture was allowed to cool, then concentrated in vacuo and the residue dissolved in ethyl acetate (25 ml) and washed with water (20 ml). The organic solution was dried (MgSO4), concentrated in vacuo and the residue purified by flash chromatography on silica gel eluting with 0-20% methanol/ethyl acetate to afford the title compound as a pale pink solid after trituation with ether (44 mg) mp 120°-126° C.

Aufarbeitung

  1. temperaturethe solution heated
  2. temperatureunder reflux for 48 h
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. dissolutionthe residue dissolved in ethyl acetate (25 ml)
  6. washwashed with water (20 ml)
  7. dry with materialThe organic solution was dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customthe residue purified by flash chromatography on silica gel eluting with 0-20% methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b88d71e3b2504237bc2f271fbd0c0ee8
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852014

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