Oxalic Acid → 1-Pentanamine, N-methyl-N-2-propynyl-, ethanedioate (1:1)

HRID 1681218Notes

Reaction equation

HRID 1681218 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:7][NH:8][CH2:9][C:10]#[CH:11].[C:12]([OH:17])(=[O:16])[C:13]([OH:15])=[O:14]>C(O)C.CCOCC>[C:12]([OH:17])(=[O:16])[C:13]([OH:15])=[O:14].[CH2:2]([N:8]([CH2:9][C:10]#[CH:11])[CH3:7])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 80571-BromopentaneHCID 96160N-methylpropyn-2-ylamine

Product 1

HCID 30725671-Pentanamine, N-methyl-N-2-propynyl-, ethanedioate (1:1)Yield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1-Bromopentane (12.1 g, 80 mmoles) and N-methylpropargylamine (11.1 g, 160 mmoles) were refluxed in absolute ethanol (75 mL) for 72 h. to give (after addition to 80 mmoles of oxalic acid in ether) the title compound in 60% yield after recrystallization from methanol-ether, m.p.=101°-103° C.

Workup

  1. customto give

Sources & evidence

ORD record
ord-d320a476430248cf959d798267ccf8fe
Source dataset
uspto-grants-1992_12
Patent number
US05169868

Reaction notes

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