o-Fluorobenzaldehyde → HCID 58786566, compound

HRID 1376022Notes

Reaction equation

HRID 1376022 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[Si]([C:14]#[N:15])(C)(C)C.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CCOCC.CO.[Zn+2].[I-].[I-]>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][N:26]([CH:4]([C:14]#[N:15])[C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[F:1])[CH2:25][CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 3

HCID 67970o-FluorobenzaldehydeHCID 82115Trimethylsilyl cyanideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 58786566HCID 58786566, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To 2-fluorobenzaldehyde (10.0 g, 80.57 mmol) in ether (10 mL) was added TMSCN (9.97 g, 100.72 mmol) followed by a catalytic amount of ZnI2 and the solution was stirred while cooling with an ice bath as necessary until the catalyst dissolved and re-precipitated out. Boc-piperazine (14.9 g, 80.57 mmol) in MeOH (60 mL) was then added and the solution was allowed to stir at reflux for 4 h and then at room temperature for 18 h. The reaction mixture was then cooled to 0° C. and the product was collected by filtration. Concentration of the mother liquor and recrystallization from methanol provided 20.0 g (78%) product.

Workup

  1. temperaturewhile cooling with an ice bath as necessary until the catalyst
  2. dissolutiondissolved
  3. customre-precipitated out
  4. stirringto stir
  5. temperatureat reflux for 4 h
  6. filtrationthe product was collected by filtration
  7. customConcentration of the mother liquor and recrystallization from methanol

Sources & evidence

ORD record
ord-6db865a941af4d25899c47899544ac97
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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