Sodium Hydroxide → HCID 23444887, compound

HRID 1840962Notes

Reaction equation

HRID 1840962 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:30])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1>O.C(O)C>[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([CH:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][O:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[C:5]([OH:30])=[O:4])[CH2:16][CH2:17]2)=[CH:22]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11440344methyl 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoate

Product 1

HCID 23444887HCID 23444887, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1.33 g (33 mmol) of sodium hydroxide in 120 mL of water was added to a suspension of 6.31 g (16.6 mmol) of 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoic acid methyl ester (prepared in Example 1, part D) in 120 mL of ethanol. This mixture was heated at 60° C. for 3 hours and the solvent was removed under reduced pressure. After addition of 50 mL of water, the crude mixture was neutralised with HCl 2N and the solid formed was isolated. After recrystallisation from acetonitrile, 2.6 g (43% of yield) of a white solid corresponding to the desired product were obtained.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionAfter addition of 50 mL of water
  3. customthe solid formed
  4. customwas isolated
  5. customAfter recrystallisation

Sources & evidence

ORD record
ord-b4ca88220d624f75b5b739ccb4623450
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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