Methyl iodide → Benzyl 3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(1-methyl-1H-indol-4-yloxymethyl)phenyl]piperidine-1-carboxylate

HRID 1712628Notes

Reaction equation

HRID 1712628 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[O:25])[CH2:20][CH:19]4[O:34][CH2:35][C:36]4[CH:37]=[CH:38][C:39]5[O:44][CH2:43][CH2:42][N:41]([CH2:45][CH2:46][CH2:47][O:48][CH3:49])[C:40]=5[CH:50]=4)=[CH:14][CH:13]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CI.[H-].[Na+].[C:55](=O)([O-])O.[Na+]>CN(C)C=O>[CH3:49][O:48][CH2:47][CH2:46][CH2:45][N:41]1[C:40]2[CH:50]=[C:36]([CH2:35][O:34][CH:19]3[CH:18]([C:15]4[CH:14]=[CH:13][C:12]([CH:11]([O:10][C:5]5[CH:6]=[CH:7][CH:8]=[C:9]6[C:4]=5[CH:3]=[CH:2][NH:1]6)[CH3:55])=[CH:17][CH:16]=4)[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:25])[CH2:20]3)[CH:37]=[CH:38][C:39]=2[O:44][CH2:43][CH2:42]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 68501215Benzyl 4-[4-(1H-indol-4-yloxymethyl)phenyl]-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Product 1

HCID 68501628Benzyl 3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(1-methyl-1H-indol-4-yloxymethyl)phenyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

The solution of 0.100 g of benzyl 4-[4-(1H-indol-4-yloxymethyl)phenyl]-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate (Example 346a), 0.0424 g of methyl iodide and 1.5 ml of N,N-dimethylformamide is admixed with stirring at −10° C. with 0.012 g of sodium hydride dispersion (60%). The reaction mixture is stirred at −10° C. for 1.5 hours, then poured onto saturated aqueous sodium hydrogencarbonate solution (45 ml) and extracted with tert-butyl methyl ether (2×75 ml). The combined organic phases are washed with 75 ml of brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a violet oil from the residue. Rt=5.90.

Workup

  1. extractionextracted with tert-butyl methyl ether (2×75 ml)
  2. washThe combined organic phases are washed with 75 ml of brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-bdcfe75e916244af924e50cd671c6153
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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