Dimethylamine → HCID 22349540, compound

HRID 1517517Notes

Reaction equation

HRID 1517517 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[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[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

5

Reactant 3

HCID 674DimethylamineHCID 1397781-Indanone, 6-bromo-HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22349540HCID 22349540, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
120 °C

Procedure

(Method 1): 6-Bromo-indan-1-one (0.23 mmol) and dimethyl-amine (0.71 mmol) were mixed in 3 ml of 1,2-dichloroethane in a process vial, which was sealed with a septum. Sodium triacetoxyborohydride (0.47 mmol) was added under argon atmosphere. The suspension was subjected to microwave irradiating conditions (CEM Discover® equipped with a CEM Explorer® automated reaction handling module). The reaction mixture was heated for 5 min at 120° C. and then cooled. The crude was evaporated to dryness and then suspended in aqueous NaHCO3 The product was extracted with CH2Cl2 and washed with aqueous NaHCO3. 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. The crude was purified by flash column chromatography (CH2Cl2-MeOH as eluents) by using a CombiFlash Companion™ system to yield the title compound (85%). MS [MH]+=240.

Workup

  1. customwhich was sealed with a septum
  2. customto microwave irradiating conditions (CEM Discover®
  3. customequipped with a CEM Explorer®
  4. customreaction handling module)
  5. temperaturecooled
  6. customThe crude was evaporated to dryness
  7. extractionwas extracted with CH2Cl2
  8. washwashed with aqueous NaHCO3
  9. extractionThe CH2Cl2 extract
  10. dry with materialwas dried with anhydrous Na2SO4
  11. filtrationfiltered
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-fb7954f790ac4c7aba73286c7db9d416
Source dataset
uspto-grants-2012_07
Patent number
US08232307B2

Reaction notes

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