2-Indanone → HCID 15078222, compound

HRID 1110446Notes

Reaction equation

HRID 1110446 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C:18]1=O.C([BH3-])#N.[Na+]>CO>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:14][CH:18]2[CH2:17][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19]2)=[CH:15][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 119832-IndanoneHCID 27238314-Benzyloxyaniline hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 15078222HCID 15078222, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.00 g (4.2 mmol, Aldrich) of 4-benzyloxyaniline hydrochloride, 555 mg (4.20 mmol, Aldrich) of 2-indanone and 132 mg (2.10 mmol) of sodium cyanoborohydride in 25 ml of MeOH was stirred over 3A molecular sieves at 25° C. for one hour. The mixture was filtered, EtOAc was added and this was washed with saturated NaHCO3, dried (MgSO4) and concentrated in vacuo. Purification via flash chromatography (silica gel, 1:5 EtOAc/petroleum ether) afforded 1.25 g (95%) of title compound as a tan solid: m.p. 72°-75° C.

Workup

  1. filtrationThe mixture was filtered
  2. additionEtOAc was added
  3. washthis was washed with saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification via flash chromatography (silica gel, 1:5 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-1d752ce6bcbc4a219490cde1b4e3a053
Source dataset
uspto-grants-1990_12
Patent number
US04975461

Reaction notes

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