Hydrochloric Acid → HCID 68501216, compound

HRID 1712350Notes

Reaction equation

HRID 1712350 reaction equation
[CH3:1][O:2][C:3]1[CH:54]=[CH:53][CH:52]=[CH:51][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][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:19][CH:18]2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([O:43]C)=[O:42])=[C:37]([O:45][CH2:46][CH2:47][CH2:48][O:49][CH3:50])[CH:36]=2)=[CH:13][CH:12]=1.O.Cl>CO.[OH-].[Na+]>[C:41]([C:38]1[CH:39]=[CH:40][C:35]([CH2:34][O:33][CH:18]2[CH:17]([C:14]3[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C:4]4[CH:51]=[CH:52][CH:53]=[CH:54][C:3]=4[O:2][CH3:1])=[CH:16][CH:15]=3)[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:24])[CH2:19]2)=[CH:36][C:37]=1[O:45][CH2:46][CH2:47][CH2:48][O:49][CH3:50])([OH:43])=[O:42]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68499319HCID 68499319, compound

Product 1

HCID 68501216HCID 68501216, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The mixture of 1.90 g of benzyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[4-methoxycarbonyl-3-(3-methoxypropoxy)benzyloxy]piperidine-1-carboxylate (Example 29a) in 15 ml of methanol and 5.0 ml of 1N NaOH is stirred at reflux over 2 hours. The reaction mixture is cooled, admixed with water (100 ml) and 2N HCl (3.0 ml), and extracted with tert-butyl methyl ether (2×100 ml). The organic phases are dried with sodium sulphate, filtered, concentrated by evaporation. This gives the crude title compound as a yellowish oil. Rt=5.72.

Workup

  1. temperatureat reflux over 2 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with tert-butyl methyl ether (2×100 ml)
  4. dry with materialThe organic phases are dried with sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b08f3e3e2944403f8324596293ec8953
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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