Sodium Hydroxide → HCID 9903877, compound

HRID 399006Notes

Reaction equation

HRID 399006 reaction equation
C(OC(=O)[N:7]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:8][CH2:9][O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13](Cl)=[CH:14][NH:15]2)(C)(C)C.[OH-:29].[Na+]>COC(O)C>[CH2:21]([NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][C:14](=[O:29])[NH:15]2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10834873HCID 10834873, compound

Product 1

HCID 9903877HCID 9903877, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-benzyl-N-[2-(3-chloro-1H-indol-4-yloxy)-ethyl]-carbamic acid tert-butyl ester (5.4 g, 13.5 mmol) in methoxyethanol (25 mL) containing 85% phosphoic acid (10 mL) was heated to 100° C. for 1 hour. The reaction was allowed to cool and then basified with 2N sodium hydroxide and extracted with methylene chloride (2×150 mL). The organic layer dried over anhydrous magnesium sulfate, filtered and chromatographed (5% methanol-methylene chloride) to afford 3.28 g of a grayish-white solid (86.1%): mp 145°-146° C. The fumarate salt was prepared in isopropanol: mp 220°-221° C.

Workup

  1. temperatureto cool
  2. extractionextracted with methylene chloride (2×150 mL)
  3. dry with materialThe organic layer dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customchromatographed (5% methanol-methylene chloride)

Sources & evidence

ORD record
ord-b883c773338e4a43a8cf46fd8b1c9f61
Source dataset
uspto-grants-1998_10
Patent number
US05817690

Reaction notes

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