Diethylamine → HCID 21485414, compound

HRID 1414940Notes

Reaction equation

HRID 1414940 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH2:12][C:13]#[CH:14])=[CH:4][C:3]=2[O:2]1.[CH2:15]([NH:17][CH2:18][CH3:19])[CH3:16].O1CC[CH2:23]OO1>O1CCOCC1>[CH2:15]([N:17]([CH2:18][CH3:19])[CH2:23][C:14]#[C:13][CH2:12][CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)[CH3:16]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 19593658CID 19593658HCID 21485755HCID 21485755, compound

Product 1

HCID 21485414HCID 21485414, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Add 5-(3,4-methylenedioxyphenyl)pent-1-yne (24.5 g) in dioxan (15 cc) to a mixture of diethylamine (16 g), trioxan (7.2 g) and cuprous chloride (0.3 g) in dioxan (20 cc) and heat the mixture at 100° for 15 hours under an atmosphere of nitrogen. Filter the cooled solution, remove the solvent and distil the residue at 0.1 mm Hg to obtain 1-diethylamino-6-(3,4-methylenedioxyphenyl)-hex-2-yne after a forerun of more volatile material.

Workup

  1. temperatureheat the mixture at 100° for 15 hours under an atmosphere of nitrogen
  2. filtrationFilter the cooled solution
  3. customremove the solvent
  4. customdistil the residue at 0.1 mm Hg

Sources & evidence

ORD record
ord-39a6a3064dad4552b55a60fbde8d5664
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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