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Triethylamine → N-(2,2-dipropoxyethyl)-N-(4-methyl-1,3-dioxolan-2-ylmethyl)amine

HRID 1111561
Notes
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Reaction equation

HRID 1111561 reaction equation
[CH2:1]([O:4][CH:5]([O:8][CH2:9][CH2:10][CH3:11])[CH2:6][NH2:7])[CH2:2][CH3:3].Br[CH2:13][CH:14]1[O:18][CH:17]([CH3:19])[CH2:16][O:15]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:9]([O:8][CH:5]([O:4][CH2:1][CH2:2][CH3:3])[CH2:6][NH:7][CH2:13][CH:14]1[O:18][CH:17]([CH3:19])[CH2:16][O:15]1)[CH2:10][CH3:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 141307cis-2-Bromomethyl-4-methyl-1,3-dioxolaneHCID 190695242,2-Dipropoxyethylamine

Product 1

HCID 22766279N-(2,2-dipropoxyethyl)-N-(4-methyl-1,3-dioxolan-2-ylmethyl)amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,2-Dipropoxyethylamine (0.11 mole), 2-bromomethyl-4-methyl-1,3-dioxolane (0.1 mole), triethylamine (20 ml) and toluene (150 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction is heated at reflux for a period of about 12 hours. After this time the reaction mixture is allowed to cool to room temperature and is filtered. The reaction mixture is then stripped of solvent and unreacted starting materials under reduced pressure to yield the desired product N-(2,2-dipropoxyethyl)-N-(4-methyl-1,3-dioxolan-2-ylmethyl)amine.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction is heated
  4. temperatureat reflux for a period of about 12 hours
  5. filtrationis filtered

Sources & evidence

ORD record
ord-5bf5ce3425e64c6da9da7c52d1a46797
Source dataset
uspto-grants-1978_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04118216

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes