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

HRID 1458615ノート

反応式

HRID 1458615 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b88d71e3b2504237bc2f271fbd0c0ee8
出典データセット
uspto-grants-1998_12
特許番号
US05852014

反応ノート

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