Potassium Iodide → Tert-butyl 3-[4-chloro-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1712291Notes

Reaction equation

HRID 1712291 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][O:7][CH:8]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH3:33])=[CH:16][CH:15]=3)[CH2:12][CH2:11][N:10]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:9]2)=[CH:4][C:3]=1[OH:43].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:51][CH2:52][CH2:53][O:54][CH3:55].[I-].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][O:7][CH:8]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH3:33])=[CH:16][CH:15]=3)[CH2:12][CH2:11][N:10]([C:34]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[O:35])[CH2:9]2)=[CH:4][C:3]=1[O:43][CH2:51][CH2:52][CH2:53][O:54][CH3:55]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1189271-Chloro-3-methoxypropaneHCID 516892Sodium BicarbonateHCID 68506109Tert-butyl 3-(4-chloro-3-hydroxybenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Product 1

HCID 68504735Tert-butyl 3-[4-chloro-3-(3-methoxypropoxy)benzyloxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The solution of 0.150 g of tert-butyl 3-(4-chloro-3-hydroxybenzyloxy)-4-{4-[3-(2-methoxy-benzyloxy)propoxy]phenyl}piperidin-1-carboxylate in 1.5 ml of N,N-dimethylformamide is admixed successively with 0.104 g of potassium carbonate, 0.082 ml of 1-chloro-3-methoxypropane and 0.004 mg of potassium iodide, and stirred at 80° C. over 20 hours. The reaction mixture is admixed with 1M aqueous sodium hydrogencarbonate solution (25 ml) and extracted with ethyl acetate (2×25 ml). The organic phases are washed with water (2×25 ml) and brine (1×25 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rt=6.44.

Workup

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

Sources & evidence

ORD record
ord-d61a7054baec447dbd600202620df24f
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

Loading…