Methanol → 6-[4-(4-Imidazol-1-ylmethylphenyl)piperidin-3-yloxymethyl]-4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 1176621ノート

反応式

HRID 1176621 の反応式
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:18][CH2:17][N:16](C(OCC4C=CC=CC=4)=O)[CH2:15][CH:14]3[O:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]4[O:39][CH2:38][CH2:37][N:36]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[C:35]=4[CH:45]=3)=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.CO.[OH-].[K+]>O1CCOCC1.O>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH:14]3[O:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]4[O:39][CH2:38][CH2:37][N:36]([CH2:40][CH2:41][CH2:42][O:43][CH3:44])[C:35]=4[CH:45]=3)=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

参加物

6

反応物 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 68504378Benzyl 4-(4-imidazol-1-ylmethylphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

生成物 1

HCID 685031956-[4-(4-Imidazol-1-ylmethylphenyl)piperidin-3-yloxymethyl]-4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

0.0978 g of benzyl 4-(4-imidazol-1-ylmethylphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate is dissolved in 3 ml of dioxane. 3 ml each of methanol and 40% KOH are added and the reaction mixture is stirred in a sealed flask at 100° C. over 5 hours. The reaction mixture is subsequently cooled to room temperature, diluted with 10 ml of water and extracted with ethyl acetate (3×30 ml). The combined organic phases are washed with 10 ml of water, then 10 ml of brine, dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F).

後処理

  1. temperatureThe reaction mixture is subsequently cooled to room temperature
  2. extractionextracted with ethyl acetate (3×30 ml)
  3. washThe combined organic phases are washed with 10 ml of water
  4. dry with material10 ml of brine, dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-573276a735bb4954a4d249e2fadb632e
出典データセット
uspto-grants-2010_11
特許番号
US07842688B2

反応ノート

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