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

HRID 1720971Notes

Reaction equation

HRID 1720971 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, 160mmoles) 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-621cb448a756477788fcfe53f27419a4
Source dataset
uspto-grants-1996_04
Patent number
US05508311

Reaction notes

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