HCID 12318585, compound → HCID 12318586, compound

HRID 1287595Notes

Reaction equation

HRID 1287595 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7]([C:14]#[N:15])=[CH:6][C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]1=2)[CH3:2].[B-].[Na+]>C(O)C>[CH2:1]([N:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]([C:14]#[N:15])[CH2:6][C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]1=2)[CH3:2]

Participants

4

Reactant 2

HCID 12318585HCID 12318585, compoundHCID 22959485Vertellus

Product 1

HCID 12318586HCID 12318586, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of approximately 49 parts of 5-ethyl-5H-dibenz[b,f]azepine-10-carbonitrile in 1,600 parts of absolute ethanol at 70°-75° is added, portionwise with stirring, 76 parts of sodium tetrahydroborate (1-). When the addition is conplete, the reaction mixture is maintained at 70°-75° with stirring for a further 1 1/2 hours, whereupon it is cooled and solvent is then removed by vacuum distillation. Approximately 2,000 parts of water is mixed with the residue. Insoluble solids are filtered out, washed on the filter with water, dried in air, and recrystallized from ethanol to give 5-ethyl-10,11-dihydro-5H-dibenz[b,f]azepine-10-carbonitrile as a yellow solid melting at 127°-129°.

Workup

  1. additionWhen the addition
  2. temperaturethe reaction mixture is maintained at 70°-75°
  3. stirringwith stirring for a further 1 1/2 hours, whereupon it
  4. temperatureis cooled
  5. customsolvent is then removed by vacuum distillation
  6. additionApproximately 2,000 parts of water is mixed with the residue
  7. filtrationInsoluble solids are filtered out
  8. washwashed on the
  9. filtrationfilter with water
  10. customdried in air
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3789350042984b5e8099bd22c48da6d0
Source dataset
uspto-grants-1976_10
Patent number
US03985730

Reaction notes

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