Acetic Acid → HCID 24693315, compound

HRID 1191008Notes

Reaction equation

HRID 1191008 reaction equation
C([BH3-])#N.[Na+].[C:5]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)#[N:6].[F:15][C:16]([F:20])([F:19])[CH2:17][NH2:18].C(O)(=O)C>CO>[F:15][C:16]([F:20])([F:19])[CH2:17][NH:18][CH2:11][C:10]1[CH:13]=[CH:14][C:7]([C:5]#[N:6])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 660424-CyanobenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 24693315HCID 24693315, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium cyanoborohydride (957 mg, 15.24 mmol) to a stirred solution of 4-cyanobenzaldehyde (500 mg, 3.81 mmol), 2,2,2-trifluoroethylamine (0.3 mL, 3.81 mmol) and acetic acid (0.44 mL, 7.62 mmol) in methanol (5 mL). Stir the mixture overnight at room temperature. Partition the mixture between 1N aqueous NaOH and DCM. Extract the aqueous phase twice with DCM. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to obtain the desired intermediate (749 mg, 92%) suitable for use without further purification. MS (ES+) m/z: 215 (M+H)+.

Workup

  1. customPartition the mixture between 1N aqueous NaOH and DCM
  2. extractionExtract the aqueous phase twice with DCM
  3. dry with materialDry the combined organic extracts over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-7161088949e94bfcbc4cecc7b8d58495
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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