Acetate → Dodecylamine

HRID 1636573Notes

Reaction equation

HRID 1636573 reaction equation
[C:1]([O-])(=O)[CH3:2].O1[CH2:10][CH2:9]OCC1.[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[N:19]([CH:21]=O)C>[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1COCC1>[CH3:17][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:9][CH2:10][CH2:1][CH2:2][CH2:21][NH2:19]

Participants

8

Reactant 4

HCID 175AcetateHCID 1140TolueneHCID 6228DimethylformamideHCID 312751,4-Dioxane

Product 1

HCID 13583Dodecylamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the acetate 11 and an amine R5R6NH in a suitable solvent such as THF, dioxane, toluene, DMF or the like, preferably THF, is treated with a suitable palladium catalyst such as tetrakis(triphenylphosphine)-palladium at a temperature of from 0° C. to about 100° C., preferably 65° C. to give the amine 12. Deprotection as above gives the amine.

Sources & evidence

ORD record
ord-72a6f30d1fea4196a39b6fa552a260f6
Source dataset
uspto-grants-2000_03
Patent number
US06034251

Reaction notes

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