3,3-Dimethylbutylamine → N-(3-fluoro-2-(3-fluoropyrrolidin-1-yl)benzylidene)-3,3-dimethylbutan-1-amine

HRID 1695950Notes

Reaction equation

HRID 1695950 reaction equation
[F:1][C:2]1[C:3]([N:10]2[CH2:14][CH2:13][CH:12]([F:15])[CH2:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:16][C:17]([CH3:22])([CH3:21])[CH2:18][CH2:19][NH2:20]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]([N:10]2[CH2:14][CH2:13][CH:12]([F:15])[CH2:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[N:20][CH2:19][CH2:18][C:17]([CH3:22])([CH3:21])[CH3:16]

Participants

4

Reactant 2

HCID 197093,3-DimethylbutylamineHCID 76602004HCID 76602004, compound

Product 1

HCID 67276676N-(3-fluoro-2-(3-fluoropyrrolidin-1-yl)benzylidene)-3,3-dimethylbutan-1-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Fluoro-2-(3-fluoropyrrolidin-1-yl)benzaldehyde (403.8 mg, 1.912 mmol) was taken in toluene (15 mL) and 3,3-dimethylbutan-1-amine (193.5 mg, 257.3 μL, 1.912 mmol) was added. The reaction mixture was refluxed overnight with a Dean Stark trap to remove the water. The reaction mixture was concentrated to give crude N-(3-fluoro-2-(3-fluoropyrrolidin-1-yl)benzylidene)-3,3-dimethylbutan-1-amine which was used directly in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed overnight with a Dean Stark trap
  2. customto remove the water
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-4847f46f260e46178c5498f3e089f6e0
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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