Trifluoroacetic acid → O-Benzyl-N-(4-cyanobutyl)hydroxylamine

HRID 1656816Notes

Reaction equation

HRID 1656816 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]#[N:29])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O)(C)(C)C.[O-]S([O-])(=O)=O.[Ca+2]>>[C:28]([CH2:27][CH2:26][CH2:25][CH2:24][NH:15][O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)#[N:29]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 24497Calcium SulfateHCID 10685938tert-Butyl benzyloxy(4-cyanobutyl)carbamate

Product 1

HCID 14078488O-Benzyl-N-(4-cyanobutyl)hydroxylamine

Procedure

N-(4-Cyanobutyl)-O-benzylhydroxylamine (5) was synthesized by adding trifluoroacetic acid (TFA, 16 mL) to (4) (2.59 g, 8.51 mmol), and the solution was stirred at room temperature for 20 minutes (Drierite tube). Excess TFA was removed by rotary evaporation, saturated NaHCO3 (50 mL) was added and the product was extracted into ether (3×50 mL). After a brine wash (50 mL), the organic extracts were concentrated to yield 1.77 g crude product. Column chromatography with 3% EtOH/CHCl3 furnished 1.31 g of (5) (75% yield): NMR δ 1.5-1.7 (m, 4 H), 2.16-2.35 (m, 2 H), 2.78-2.98 (m, 2 H), 4.66 (s, 2 H), 5.45 (br s, 1 H), 7.28 (s, 5 H). Anal. calcd. for C12H16N2O: C, 70.56; H, 7.90. Found: C, 70.51; H, 7.91.

Workup

  1. customExcess TFA was removed by rotary evaporation, saturated NaHCO3 (50 mL)
  2. additionwas added
  3. extractionthe product was extracted into ether (3×50 mL)
  4. washAfter a brine wash (50 mL)
  5. concentrationthe organic extracts were concentrated
  6. customto yield 1.77 g crude product

Sources & evidence

ORD record
ord-2ab58d8ca4644d68aa734f1529101b92
Source dataset
uspto-grants-1993_10
Patent number
US05254724

Reaction notes

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