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Benzylamine → Benzyl[2-(diethylamino)ethyl]amine

HRID 81456
Notes
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Reaction equation

HRID 81456 reaction equation
Cl.[CH2:2]([N:4]([CH2:8][CH3:9])[CH2:5][CH2:6]Cl)[CH3:3].[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(O)(C)(C)C>[CH2:10]([NH:17][CH2:6][CH2:5][N:4]([CH2:2][CH3:3])[CH2:8][CH3:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 133631-Chloro-2-(diethylamine)ethane hydrochloride

Product 1

HCID 296044Benzyl[2-(diethylamino)ethyl]amineYield 47%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-(diethylamino)-ethyl chloride hydrochloride (1 g, 5.81 mmol) and benzylamine (1.3 ml, 11.62 mmol) were dissolved in t-butanol (40 ml), triethylamine (3.2 ml, 23.24 mmol) was added thereto, and the resulting solution was refluxed for 12 hours. The solution was cooled to room temperature, and distilled under a reduced pressure to remove the solvent. The resulting solid was removed by filtration under a reduced pressure, and the residual solution was extracted with ethylacetate The separated organic layer was washed with saturated sodium bicarbonate aqueous solution, dried over magnesium sulfate, filtered and distilled under a reduced pressure to obtain the title compound 560 mg (yield: 47%).

Workup

  1. temperaturethe resulting solution was refluxed for 12 hours
  2. distillationdistilled under a reduced pressure
  3. customto remove the solvent
  4. customThe resulting solid was removed by filtration under a reduced pressure
  5. extractionthe residual solution was extracted with ethylacetate The separated organic layer
  6. washwas washed with saturated sodium bicarbonate aqueous solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-2aa2f080a6e7462a950dda5e0d915cc8
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846699B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes