Methylamine → 4-[1,3]Dioxan-2-yl-N-methyl-butyramide

HRID 33224Notes

Reaction equation

HRID 33224 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O.CN.Cl.[CH3:16][N:17](C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1>ClCCl>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][CH2:9][C:10]([NH:17][CH3:16])=[O:12]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69311668HCID 69311668, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 693155474-[1,3]Dioxan-2-yl-N-methyl-butyramideYield 113.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-[1,3]dioxan-2-yl-butyric acid (2.55 g, 0.015 mol) in dichloromethane (200 ml) was added methylamine (2M in THF, 8.1 ml, 0.016 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.09 g, 0.016 mol) and hydroxybenzotriazole (2.16 g, 0.016 mol) and the mixture stirred at room temperature overnight. The organic layer was washed with saturated sodium bicarbonate solution (200 ml) and the aqueous layer extracted with dichloromethane (4×50 ml). The combined organics were dried (Na2SO4) and evaporated to give a colourless oil (3.2 g)

Workup

  1. washThe organic layer was washed with saturated sodium bicarbonate solution (200 ml)
  2. extractionthe aqueous layer extracted with dichloromethane (4×50 ml)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-45ea3b8591ff4b7bb3fddd7fcac0af8f
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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