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Toluene → Diethyl 1,4-dihydro-4-(2-trifluoromethylphenyl)-2,6-dimethyl-1-(2-[N,N-bis-(methoxyethyl)]aminoethyl)-3,5-pyridine dicarboxylate

HRID 463533
Notes
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Reaction equation

HRID 463533 reaction equation
[H-].[Na+].[F:3][C:4]([F:30])([F:29])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([CH3:22])[NH:14][C:13]([CH3:23])=[C:12]1[C:24]([O:26][CH2:27][CH3:28])=[O:25].C1(C)C=CC=CC=1.Cl[CH2:39][CH2:40][N:41]([CH2:46][CH2:47][O:48][CH3:49])[CH2:42][CH2:43][O:44][CH3:45]>CN(C=O)C>[F:30][C:4]([F:29])([F:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[C:12]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:13]([CH3:23])[N:14]([CH2:39][CH2:40][N:41]([CH2:46][CH2:47][O:48][CH3:49])[CH2:42][CH2:43][O:44][CH3:45])[C:15]([CH3:22])=[C:16]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 1680891,4-Dihydro-2,6-dimethyl-4-(2-(trifluoromethyl)phenyl)-3,5-pyridinedicarboxylic acid diethyl esterHCID 156595712-chloro-N,N-bis(methoxyethyl)ethylamine

Product 1

HCID 20281063Diethyl 1,4-dihydro-4-(2-trifluoromethylphenyl)-2,6-dimethyl-1-(2-[N,N-bis-(methoxyethyl)]aminoethyl)-3,5-pyridine dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of sodium hydride (5.2 gms.; 0.11 mole) (50% suspension mineral oil) in 100 ml of dry distilled DMF is added a solution of diethyl 1,4-dihydro-4-(2-trifluoromethylphenyl)-2,6-dimethyl-3,5-pyridine dicarboxylate (39.7 gms.; 0.1 mole) in 150 ml of DMF. After the gassing has ceased, the reaction mixture is heated on a water bath for 1 hour and then is cooled to 50° C. and to the hot solution is added a toluene solution of 2-chloro-N,N-bis(methoxyethyl)ethylamine. The reaction mixture is heated at 100°-110° C. for a period of 8 hours and then cooled. The unreacted NaH and NaCl is filtered off and the solvent removed from the filtrate. The residue is extracted with hot hexane which, on cooling, affords the desired product. Recrystallization from heptane yields the pure product.

Workup

  1. customof dry
  2. distillationdistilled DMF
  3. temperaturethe reaction mixture is heated on a water bath for 1 hour
  4. temperatureThe reaction mixture is heated at 100°-110° C. for a period of 8 hours
  5. temperaturecooled
  6. filtrationThe unreacted NaH and NaCl is filtered off
  7. customthe solvent removed from the filtrate
  8. extractionThe residue is extracted with hot hexane which
  9. temperatureon cooling

Sources & evidence

ORD record
ord-19e44a28db16498895aff6545ae620b0
Source dataset
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04520131

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes