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

HRID 1176621Notes

Reaction equation

HRID 1176621 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-573276a735bb4954a4d249e2fadb632e
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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