Tetrahydrofuran → 2-(4-{4-[3-(2-Methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxymethyl)-1-(3-methoxypropyl)-1H-indole

HRID 1712295Notes

Reaction equation

HRID 1712295 reaction equation
CS(N1C2C(=CC=CC=2)C=C1[CH2:14][O:15][CH:16]1[CH:21]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[O:40][CH3:41])=[CH:24][CH:23]=2)[CH2:20][CH2:19][N:18](C(OCC2C=CC=CC=2)=O)[CH2:17]1)(=O)=O.[F-].C([N+:57]([CH2:66][CH2:67][CH2:68][CH3:69])([CH2:62][CH2:63][CH2:64][CH3:65])[CH2:58][CH2:59][CH2:60]C)CCC.[O:70]1CCC[CH2:71]1>>[CH3:41][O:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][O:32][CH2:31][CH2:30][CH2:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([CH:21]2[CH2:20][CH2:19][NH:18][CH2:17][CH:16]2[O:15][CH2:14][C:66]2[N:57]([CH2:58][CH2:59][CH2:60][O:70][CH3:71])[C:62]3[C:68]([CH:67]=2)=[CH:69][CH:65]=[CH:64][CH:63]=3)=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 68499233HCID 68499233, compound

Product 1

HCID 685004622-(4-{4-[3-(2-Methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxymethyl)-1-(3-methoxypropyl)-1H-indole

Procedure

The solution of 0.160 g of benzyl 3-(1-methanesulphonyl-1H-indol-2-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 11 ml of tetrahydrofuran is admixed with 0.44 ml of tetrabutylammonium fluoride solution (1M in tetrahydrofuran) and stirred at reflux over 20 hours. The reaction mixture is cooled, poured onto brine (40 ml) and extracted with ethyl acetate (2×40 ml). The organic phases are washed with brine (1×40 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.18 (1:2 EtOAc-heptane); Rt=26.90 (II).

Workup

  1. temperatureat reflux over 20 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto brine (40 ml)
  4. extractionextracted with ethyl acetate (2×40 ml)
  5. washThe organic phases are washed with brine (1×40 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-71b7c1c2ece549f69853ca721e38e226
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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