Butanal → HCID 59164567, compound

HRID 1441691Notes

Reaction equation

HRID 1441691 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([CH3:19])[CH:12]=1.C(N(CC)CC)C.[CH:27](=O)[CH2:28][CH2:29][CH3:30].[BH4-].[Na+]>CO.C(OCC)(=O)C>[CH2:27]([NH:8][CH2:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([CH3:19])[CH:12]=1)[CH2:28][CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 261ButanalHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 68406062HCID 68406062, compound

Product 1

HCID 59164567HCID 59164567, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

138 mg 4-(2-Amino-ethyl)-2-methyl-benzonitrile trifluoro acetate, 210 μl triethylamine and 50 μl Butyraldehyde were dissolved in 5 ml methanol. 150 mg molecular sieves 4 Angström were added and the mixture was stirred at room temperature overnight. Then 21 mg sodium borohydride were added and the mixture was stirred for an additional hour at room temperature. 50 ml ethyl acetate were added, and the reaction was quenched by addition of 0.5 ml water. The reaction mixture was filtered through a pad of celite and MgSO4. The filtrate was evaporated in vacuo to provide 230 mg crude 4-(2-Butylamino-ethyl)-2-methyl-benzonitrile, impurified with salts. This material was used without further purification.

Workup

  1. addition150 mg molecular sieves 4 Angström were added
  2. stirringthe mixture was stirred for an additional hour at room temperature
  3. customthe reaction was quenched by addition of 0.5 ml water
  4. filtrationThe reaction mixture was filtered through a pad of celite and MgSO4
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c5ce579f81fc4e6daf1195b11502bc02
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

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