Ethyl ketone → HCID 28419977, compound

HRID 2189294Notes

Reaction equation

HRID 2189294 reaction equation
[CH3:1][CH2:2][C:3](=O)[CH2:4][CH3:5].[CH2:7]([NH2:10])[CH:8]=[CH2:9].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:7]([NH:10][CH:3]([CH2:4][CH3:5])[CH2:2][CH3:1])[CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 7288Ethyl ketoneHCID 7853AllylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 28419977HCID 28419977, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-pentanone (1 g, 11.6 mmol) in anhydrous 1,2-dichloroethane (45 mL) is added allylamine (0.872 mL, 11.6 mmol) followed by NaBH(OAc)3 (3.44 g, 16.3 mmol) at ambient temperature. The reaction mixture is stirred at room temperature overnight. The reaction mixture is quenched with 1N NaOH and extracted with dichloromethane. The extract is dried over Na2SO4 and concentrated in vacuo to give 1.27 g of allyl-(1-ethyl-propyl)-amine. The crude product is used as it is.

Workup

  1. customThe reaction mixture is quenched with 1N NaOH
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract is dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f70fb2250a6d45208655b65f9dc0cc1f
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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