Dibenzylamine → HCID 71254443, compound

HRID 539960Notes

Reaction equation

HRID 539960 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:16]1[CH2:20][CH2:19][C:18](=O)[CH2:17]1.C[Si]([C:26]#[N:27])(C)C.C(=O)(O)[O-].[Na+]>C(O)(=O)C.C(OCC)(=O)C.O>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:18]1([C:26]#[N:27])[CH2:19][CH2:20][O:16][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 7656DibenzylamineHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 5293923-Oxotetrahydrofuran

Product 1

HCID 71254443HCID 71254443, compoundYield 9.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled solution of dibenzylamine (31.9 g, 162 mmol) in acetic acid (100 mL) at 0° C., dihydrofuran-3(2H)-one (7.0 g, 81 mmol) was added followed by trimethylsilyl-formonitrile (14.4 g, 145.8 mmol). After being stirred at room temperature for 16 hours, the reaction mixture was poured into water (100 mL), adjusted to pH 7 with sodium bicarbonate, exacted with ethyl acetate (100 mL×2). The combined organic layers were washed with brine (150 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography to afford 2.2 g of the desired product (yield was 9.28%).

Workup

  1. washThe combined organic layers were washed with brine (150 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f62d86c3347548a08ae54bc166b89069
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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