Benzylamine → HCID 21581542, compound

HRID 2408342Notes

Reaction equation

HRID 2408342 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Si]([C:11]#[N:12])(C)(C)C.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([NH:20][C:1]1([C:11]#[N:12])[CH2:5][CH2:4][CH2:3][CH2:2]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 8452CyclopentanoneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 21581542HCID 21581542, compoundYield 85%

Procedure

7 g of cyclopentanone are solubilized in 10 mL of benzylamine. The reaction mixture is stirred for 30 mins under argon and at RT. 12.75 mL of TMSCN are added dropwise and then stirred for 1 h. They are dry evaporated. They are purified by flash chromatography on silica gel (heptane/EtOAc 99:1, to heptane/EtOAc 65:35). 14.15 g (yield=85%) of 1-(benzylamino)cyclopentanecarbonitrile are obtained as a colorless oil.

Workup

  1. stirringstirred for 1 h
  2. customThey are dry
  3. customevaporated
  4. customThey are purified by flash chromatography on silica gel (heptane/EtOAc 99:1, to heptane/EtOAc 65:35)

Sources & evidence

ORD record
ord-dfe0af339f434e9896d9b4aa0b898468
Source dataset
uspto-grants-2014_08
Patent number
US08815853B2

Reaction notes

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