2-Indanone → HCID 15078222, compound

HRID 1110451Notes

Reaction equation

HRID 1110451 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.Cl.[CH2:12]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH3-]C#N.[Na+]>CO>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([NH:24][CH:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:1]2)=[CH:25][CH:26]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 119832-IndanoneHCID 27238314-Benzyloxyaniline hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 15078222HCID 15078222, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2.00 g (15.1 mmol, Aldrich) of 2-indanone and 3.57 g (15.1 mmol, Aldrich) of 4-benzyloxyaniline hydrochloride in 30 ml of methanol was stirred over 3Å molecular sieves at 25° C. and 476 mg (7.57 mmol, Aldrich) of NaBH3CN was added in four portions. The resulting yellow solution was stirred at 25° C. for approximately two hours, filtered and the filtrate added to saturated NaHCO3. This was extracted with EtOAc twice, the organic layers were combined, dried (MgSO4) and concentrated in vacuo. Purification via flash chromatography (silica gel, 1:7 EtOAc/petroleum ether) afforded 3.02 g (64%) of title compound as an off-white solid: m.p. 74°-76° C.

Workup

  1. filtrationfiltered
  2. additionthe filtrate added to saturated NaHCO3
  3. extractionThis was extracted with EtOAc twice
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification via flash chromatography (silica gel, 1:7 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-a3d0afcd069a449f9306fb02838209c5
Source dataset
uspto-grants-1990_12
Patent number
US04975461

Reaction notes

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