Sodium Hydroxide → HCID 16059210, compound

HRID 1716414Notes

Reaction equation

HRID 1716414 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[NH:27][C:26]3=O)[CH2:21][CH2:20]2)=[O:18])=[C:9]1[CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:38])=O.[OH-].[Na+]>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]3[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[N:27]=[C:26]3[Cl:38])[CH2:21][CH2:20]2)=[O:18])=[C:9]1[CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 16059411HCID 16059411, compound

Product 1

HCID 16059210HCID 16059210, compoundYield 68%

Conditions

Temperature
100 °C

Procedure

A mixture of 0.45 g (0.97 mmol) of 1-[1-(1-benzyl-2-methyl-1H-indole-3-carbonyl)-piperidin-4-yl]-1,3-dihydro-benzoimidazol-2-one (the preparation of which is described hereinafter) and phosphorus oxychloride (6 ml) was stirred at 100° C. for 2 hours and then allowed to cool. The reaction mixture was poured into ice-cold water, 10N NaOH was added until the ph=14, and the mixture was extracted with AcOEt. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Re-crystallization in Et2O afforded 0.32 g (68%) of (1-benzyl-2-methyl-1H-indol-3-yl)-[4-(2-chloro-benzoimidazol-1-yl)-piperidin-1-yl]-methanone as white crystals. ES-MS m/e (%): 483.6 (M+H+).

Workup

  1. customthe preparation of which
  2. temperatureto cool
  3. additionwas added until the ph=14
  4. extractionthe mixture was extracted with AcOEt
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2236c8e64e6744788026d65fa4602474
Source dataset
uspto-grants-2010_09
Patent number
US07803815B2

Reaction notes

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