Butylamine → HCID 178448983, compound

HRID 254534Notes

Reaction equation

HRID 254534 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=O.[CH2:11]([NH2:15])[CH2:12][CH2:13][CH3:14]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:11](/[N:15]=[CH:4]/[C:3]1[C:2]([F:1])=[CH:9][CH:8]=[CH:7][C:6]=1[F:10])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 2

HCID 8007ButylamineHCID 1362842,6-Difluorobenzaldehyde

Product 1

HCID 178448983HCID 178448983, compoundYield 86.1%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 25.4 g (179 mmol) 2,6-difluorobenzaldehyde, 19.5 ml (197 mmol) N-butylamine and 0.68 g (3.57 mmol) p-toluenesulfonic acid in 120 ml toluene was heated in a Dean-Stark apparatus at reflux for 3 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed sequentially with water (twice) and with saturated brine. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound 30.4 g (86%) as a brown oil which was used in the next step without further purification. MS (ISP): 198.3 ([M+H]+, 100%).

Workup

  1. temperaturewas heated in a Dean-Stark apparatus
  2. temperatureat reflux for 3 hours
  3. washwashed sequentially with water (twice) and with saturated brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80a29760f07746cd8884e0fca3e57ba8
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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