Sodium hydride → HCID 68502153, compound

HRID 1176225Notes

Reaction equation

HRID 1176225 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][O:11][CH:12]3[CH:17]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=5[O:36][CH3:37])=[CH:20][CH:19]=4)[CH2:16][CH2:15][N:14]([C:38]([O:40][CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[O:39])[CH2:13]3)[CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Cl[CH2:51][CH2:52][CH2:53][O:54][CH3:55]>CN1C(=O)N(C)CCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:37][O:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][O:28][CH2:27][CH2:26][CH2:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([CH:17]2[CH2:16][CH2:15][N:14]([C:38]([O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[O:39])[CH2:13][CH:12]2[O:11][CH2:10][C:7]2[CH:8]=[C:9]3[C:4]([CH:3]=[CH:2][N:1]3[CH2:51][CH2:52][CH2:53][O:54][CH3:55])=[CH:5][CH:6]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1189271-Chloro-3-methoxypropaneHCID 68501735HCID 68501735, compound

Product 1

HCID 68502153HCID 68502153, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

The solution of 0.155 g of benzyl 3-(1H-indol-6-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 1.5 ml of DMPU is admixed with stirring at room temperature with 0.015 g of sodium hydride dispersion (60%). The mixture is stirred over 5 minutes and subsequently admixed with 0.081 ml of 1-chloro-3-methoxypropane and 0.007 g of tetrabutylammonium iodide. The reaction mixture is stirred at room temperature over 24 hours, cooled and poured onto water (20 ml). The mixture is extracted with tert-butyl methyl ether (2×20 ml). The organic phases are washed successively with water (2×20 ml) and brine (1×20 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.25 (1:1 EtOAc-heptane); Rt=27.51 (II).

Workup

  1. stirringThe reaction mixture is stirred at room temperature over 24 hours
  2. temperaturecooled
  3. additionpoured onto water (20 ml)
  4. extractionThe mixture is extracted with tert-butyl methyl ether (2×20 ml)
  5. washThe organic phases are washed successively with water (2×20 ml) and brine (1×20 ml)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f9fcc929c96b48039d055750f706d52b
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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