Dimethylformamide → HCID 54477862, compound

HRID 1287596Notes

Reaction equation

HRID 1287596 reaction equation
O1CCCC1.[H-].[Na+].Cl.Cl[CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14].[CH2:17]([N:19]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH:23](C#N)[CH2:22][C:21]2[CH:32]=[CH:33][CH:34]=[CH:35][C:20]1=2)[CH3:18].[CH3:36][N:37](C)C=O>>[CH2:13]([N:12]([CH2:15][CH3:16])[CH2:11][CH2:10][CH:22]1[C:21]2[CH:32]=[CH:33][CH:34]=[CH:35][C:20]=2[N:19]([CH2:17][CH3:18])[C:25]2[CH:26]=[CH:27][CH:28]=[C:29]([C:36]#[N:37])[C:24]=2[CH2:23]1)[CH3:14]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 24758Sodium hydride2×HCID 12318586HCID 12318586, compound

Product 1

HCID 54477862HCID 54477862, compound

Procedure

To a mixture of 3 parts of 5-ethyl-10,11-dihydro-5H-dibenz[b,f]azepine110-carbonitrile with approximately 30 parts of tetrahydrofuran and 5 parts of N,N-dimethylformamide is added 6 parts of sodium hydride, followed by 3 parts of 2-chloro-N,N-diethylethanamine hydrochloride. The resultant mixture is heated at the boiling point under reflux with stirring while thin layer chromatography is employed to monitor the reaction which ensues, additional sodium hydride being introduced as indicated thereby. After approximately 3 hours, when no 5-ethyl-10,11-dihydro-5H-dibenz[b,f]azepine-10-carbonitrile is detectable, excess sodium hydride is destroyed by adding water until evolution of hydrogen ceases, whereupon solvent is removed by vacuum distillation. The residue is partitioned between ether and water. The ethereal phase, dried over magnesium sulfate and stripped of solvent by vacuum distillation, affords 10-[2-(diethylamino)ethyl]-5-ethyl-10,11-dihydro-5H-dibenz[b,f]azepine-l-carbonitrile as a clear yellow oil.

Workup

  1. temperatureunder reflux
  2. customthe reaction which
  3. customexcess sodium hydride is destroyed
  4. additionby adding water until evolution of hydrogen ceases
  5. customwhereupon solvent is removed by vacuum distillation
  6. customThe residue is partitioned between ether and water
  7. dry with materialThe ethereal phase, dried over magnesium sulfate
  8. distillationstripped of solvent by vacuum distillation

Sources & evidence

ORD record
ord-f478ad06b8744a45a1845385931399fb
Source dataset
uspto-grants-1976_10
Patent number
US03985730

Reaction notes

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