Dimethylformamide → Tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]-phenyl}-3-{2-[2-(3-methylsulphanylpropyl)phenoxy]ethoxy}piperidine-1-carboxylate

HRID 1176322Notes

Reaction equation

HRID 1176322 reaction equation
[CH3:1][O:2][C:3]1[CH:56]=[CH:55][CH:54]=[CH:53][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][CH2:32][O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH2:40][CH2:41]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:13][CH:12]=1.[CH3:57][S-:58].[Na+].[CH3:60]N(C)C=O>COC(C)(C)C>[CH3:1][O:2][C:3]1[CH:56]=[CH:55][CH:54]=[CH:53][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][CH2:32][O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH2:40][CH2:41][CH2:57][S:58][CH3:60])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 86609986Tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-(2-{2-[2-(toluene-4-sulphonyloxy)ethyl]phenoxy}-ethoxy)piperidine-1-carboxylate

Product 1

HCID 68571833Tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]-phenyl}-3-{2-[2-(3-methylsulphanylpropyl)phenoxy]ethoxy}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 0.50 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-(2-{2-[2-(toluene-4-sulphonyloxy)ethyl]phenoxy}ethoxy)piperidine-1-carboxylate (Example 26b) and 0.55 g of sodium methanethiolate in 5 ml of N,N-dimethylformamide is stirred at 90° C. over 1 hour. The reaction mixture is cooled to room temperature, diluted with tert-butyl methyl ether, washed with saturated aqueous sodium bicarbonate solution, dried with sodium sulphate and concentrated by evaporation. The crude title compound is obtained as a colourless oil from the residue. Rt=6.53.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. dry with materialdried with sodium sulphate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-3c41122527f44880af51c7d4fc156fce
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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