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

HRID 609610

Reaction equation

HRID 609610 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A stirred solution of N-(4-piperidinylmethyl) 3,4-dihydro-2H-[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 (44mg) mp 120-126° C.

Workup

  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

Sources & evidence

ORD record
ord-6f7ffc8c04fe43f9bfd3454885448099
Source dataset
uspto-grants-1999_12
Patent number
US05998409

Linked notes

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