Chloroform → 8-Chloro-6,11-dihydro-5H-dibenz[b,e]azepine

HRID 1388901Notes

Reaction equation

HRID 1388901 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(Cl)(Cl)Cl.[Cl:11][C:12]1[CH:27]=[CH:26][C:15]2[CH2:16][C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[NH:19][C:20](=O)[C:14]=2[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:11][C:12]1[CH:27]=[CH:26][C:15]2[CH2:16][C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[NH:19][CH2:20][C:14]=2[CH:13]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 13364646HCID 13364646, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 133646478-Chloro-6,11-dihydro-5H-dibenz[b,e]azepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1.5 g lithium aluminium hydride in 100 ml tetrahydrofuran is added with ice cooling first 1.05 ml chloroform and thereafter portionwise 3.0 g of 8-chloro-5,6-dihydro-11H-dibenz[b,e]azepin-6-one. The mixture is stirred at room temperature for 15 hours. To the mixture is then added dropwise under ice cooling 9.0 ml of a saturated solution of potassium carbonate. The precipitate is filtered off and washed with ether. The filtrate is then evaporated and the residue recrystallised from methylene chloride/ether/petroleum ether to give the heading compound, m.p. 132°-135°.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with ether
  3. customThe filtrate is then evaporated
  4. customthe residue recrystallised from methylene chloride/ether/petroleum ether
  5. customto give the heading compound, m.p. 132°-135°

Sources & evidence

ORD record
ord-af8ac39ac91b458b935988b3f9619988
Source dataset
uspto-grants-1984_02
Patent number
US04434171

Reaction notes

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