Acetic Acid → HCID 25154364, compound

HRID 1517520Notes

Reaction equation

HRID 1517520 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][CH2:13][C:14]3=O)=[CH:10][CH:9]=2)[C:4]([CH3:18])=[N:3]1.[CH3:19][NH:20][CH3:21].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:19][N:20]([CH3:21])[CH:14]1[C:15]2[C:11](=[CH:10][CH:9]=[C:8]([C:5]3[C:4]([CH3:18])=[N:3][N:2]([CH3:1])[C:6]=3[CH3:7])[CH:16]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 58173147HCID 58173147, compound

Product 1

HCID 25154364HCID 25154364, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

(Method 1): 6-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-indan-1-one (0.20 mmol), dimethyl-amine (2.31 mmol) and acetic acid (0.020 mmol) were mixed in 3 ml of MeOH in a process vial, which was sealed with a septum. Sodium cyanoborohydride (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 1 h at 120° C. 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 dimethyl-[6-(1,3,5-trimethyl-1H-pyrazol-4-yl)-indan-1-yl]-amine. The crude was purified by flash column chromatography (CH2Cl2-MeOH as eluents) by using a CombiFlash Companion™ system to yield the base of the title compound. The obtained product was diluted in ethyl acetate (5 mL) and a solution of hydrogen chloride 2,0 M in diethylether was added. The resulting precipitate was filtered and dried under vacuum to yield the title compound dimethyl-[6-(1,3,5-trimethyl-1H-pyrazol-4-yl)-indan-1-yl]-amine dihydrochloride (83%). MS [MH]+=270.

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. extractionThe product was extracted with CH2Cl2
  8. washwashed with water
  9. extractionThe CH2Cl2 extract
  10. dry with materialwas dried with anhydrous Na2SO4
  11. filtrationfiltered
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-2b2212ccb888484e920afb08f72d377b
Source dataset
uspto-grants-2012_07
Patent number
US08232307B2

Reaction notes

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