Acetic Acid → HCID 22349540, compound

HRID 1517518Notes

Reaction equation

HRID 1517518 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=O)=[CH:4][CH:3]=1.[CH3:12][NH:13][CH3:14].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[N:13]([CH3:14])[CH3:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 1397781-Indanone, 6-bromo-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 22349540HCID 22349540, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Method 2): 6-Bromo-indan-1-one (0.58 mmol) was dissolved in MeOH. Dimethyl-amine (3.7 mmol), acetic acid (0.059 mmol) and sodium cyanoborohydride (1.74 mmol) were added under argon atmosphere. The suspension was refluxed overnight and then cooled. The crude was evaporated to dryness and then suspended in water. The product was extracted with CH2Cl2 and washed with water. The CH2Cl2 extract was dried with anhydrous Na2SO4, filtered and evaporated to dryness to give the crude product (6-bromo-indan-1-yl)-dimethyl-amine (80% conversion LC-MS). The crude product was used in the next synthetic step (Suzuki coupling), without further purification.

Workup

  1. temperatureThe suspension was refluxed overnight
  2. temperaturecooled
  3. customThe crude was evaporated to dryness
  4. extractionThe product was extracted with CH2Cl2
  5. washwashed with water
  6. extractionThe CH2Cl2 extract
  7. dry with materialwas dried with anhydrous Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-888d11ae4ced4192ad252204f83621cb
Source dataset
uspto-grants-2012_07
Patent number
US08232307B2

Reaction notes

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