Dipropylamine → HCID 86613887, compound

HRID 598095Notes

Reaction equation

HRID 598095 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[Br:8][C:9]1[N:14]=[C:13]([CH:15]=O)[CH:12]=[CH:11][CH:10]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[Br:8][C:9]1[N:14]=[C:13]([CH2:15][N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 8902DipropylamineHCID 27570096-Bromopyridine-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86613887HCID 86613887, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Dipropylamine (7.4 mL, 54 mmol) and 6-bromopyridine-2-carbaldehyde (5.0 g, 27 mmol) were dissolved in 1,2-dichloroethane (50 mL). 2 drops of glacial acetic acid was added followed by sodium triacetoxyborohydride (11.4 g, 54 mmol). The reaction was stirred at 50° C. for 1 h. The reaction was cooled and quenched with water. The solution was diluted with saturated sodium bicarbonate and extracted with ethyl acetate (3 times). The organic layers were dried over magnesium sulfate, filtered and concentrated. Flash chromatography gave 5.34 g (73% yield) of product.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with water
  3. additionThe solution was diluted with saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate (3 times)
  5. dry with materialThe organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-69cd6ed1cc584df3a98171dd07898104
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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