alpha-Chloro-m-nitrotoluene → HCID 68572892, compound

HRID 1176226Notes

Reaction equation

HRID 1176226 reaction equation
[OH:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:3]1.[N+:38]([C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][CH:48]=1)[CH2:44]Cl)([O-:40])=[O:39].[H-].[Na+].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:27][O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][O:18][CH2:17][CH2:16][CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([CH:7]2[CH2:6][CH2:5][N:4]([C:28]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:29])[CH2:3][CH:2]2[O:1][CH2:44][C:43]2[CH:46]=[CH:47][CH:48]=[C:41]([N+:38]([O-:40])=[O:39])[CH:42]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 12078alpha-Chloro-m-nitrotolueneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 68499596Benzyl 3-hydroxy-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Product 1

HCID 68572892HCID 68572892, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

The solution of 0.512 g of benzyl 3-hydroxy-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate and 0.355 g of 3-nitrobenzyl chloride in 3.0 ml of N,N-dimethylformamide is admixed with stirring at −10° C. with 0.022 g of sodium hydride dispersion (60%). The reaction mixture is stirred at −10° C. over 2.5 hours, then poured onto 1M aqueous sodium hydrogencarbonate solution (25 ml) and extracted with ethyl acetate (2×25 ml). The organic phases are washed successively with water (2×25 ml) and brine (1×25 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.35 (1:1 EtOAc-heptane); Rt=5.94.

Workup

  1. extractionextracted with ethyl acetate (2×25 ml)
  2. washThe organic phases are washed successively with water (2×25 ml) and brine (1×25 ml)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-19fb6f8e73144785837423d4f1a7a2ee
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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