Potassium Hydroxide → 2-Amino-5,6-bis(methoxymethyl)indane

HRID 2061511Notes

Reaction equation

HRID 2061511 reaction equation
[OH-].[K+].FC(F)(F)C([NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:20][O:21][CH3:22])=[C:13]([CH2:17][O:18][CH3:19])[CH:14]=2)[CH2:9]1)=O>O.CO>[NH2:7][CH:8]1[CH2:9][C:10]2[C:15](=[CH:14][C:13]([CH2:17][O:18][CH3:19])=[C:12]([CH2:20][O:21][CH3:22])[CH:11]=2)[CH2:16]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 224992202-(Trifluoroacetylamino)-5,6-bis(methoxymethyl)indane

Product 1

HCID 668228442-Amino-5,6-bis(methoxymethyl)indane

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (150 mg, 2.60 mmol) in water (0.5 ml) is added to a solution of 2-(trifluoroacetylamino)-5,6-bis(methoxymethyl)indane (240 mg, 0.75 mmol) in methanol (3 mL) and the mixture is heated at reflux for 2.5 hours. The solvent was removed in vacuo and the residue is partitioned between aqueous sodium hydroxide (10 mL) and ethyl acetate (20 mL). The organic extract is dried (MgSO4) and the solvent is removed in vacuo to leave the product as a dark oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 2.5 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue is partitioned between aqueous sodium hydroxide (10 mL) and ethyl acetate (20 mL)
  5. extractionThe organic extract
  6. dry with materialis dried (MgSO4)
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-8080787faf2c48d8902911be7c249cb7
Source dataset
uspto-grants-2012_10
Patent number
US08283362B2

Reaction notes

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