Pyridine → Decylamine

HRID 247898Notes

Reaction equation

HRID 247898 reaction equation
C(Cl)Cl.C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+].B#B.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(COC)OC.O1CCOCC1.O1CCCC1.CCOCC.C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH3:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH2:15]

Participants

12

Reactant 5

HCID 1049PyridineHCID 6212ChloroformHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 6328200Diboron

Product 1

HCID 8916Decylamine

Reagents, catalysts & solvents 6

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolventHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

An alternative synthesis of 10 can be accomplished by first reacting the amine 6 with a suitable carboxylic acid (as a melt) or with an acid chloride in an inert solvent such as methylene chloride, chloroform, ether or toluene and with a base such as triethylamine, pyridine or sodium bicarbonate present. The intermediate amide is then reduced with a suitable reagent such as diborane in an inert solvent such as ether, tetrahydrofuran (THF), dioxane or dimethoxyethane to afford the desired amine 10.

Sources & evidence

ORD record
ord-bfd6fac7dafe43f0b928d2622cad077d
Source dataset
uspto-grants-1993_05
Patent number
US05208252

Reaction notes

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