Boron tribromide → HCID 20441344, compound

HRID 1632923Notes

Reaction equation

HRID 1632923 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:15]=[CH:14][C:13]2[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]3[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][C:10]=3[C:9]=2[CH:8]=1>ClCCl>[OH:6][C:7]1[CH:15]=[CH:14][C:13]2[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]3[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][C:10]=3[C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 20441345HCID 20441345, compound

Product 1

HCID 20441344HCID 20441344, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.58 g of boron tribromide in 10 ml dichloromethane is added dropwise at -60° to a solution of 2 g 1,2,3,4,5,6-hexahydro-9-methoxy-3-methyl-6-phenyl-azepino[4,5-b]indole in 20 ml dichloromethane. The mixture is stirred at -60° for 1 hour and a dark oil separates out. The mixture is concentrated under reduced pressure and the residual oil is treated with 30 ml ethanol. The mixture is brought to reflux over 30 minutes and the hydrobromide of the title compound crystallizes out. The salt is then filtered off, washed with a little alcohol and partitioned between dichloromethane and aqueous ammonia to form the free base. The organic phase is separated off, washed with water, dried over sodium sulphate, filtered and concentrated under reduced pressure. The oily residue is dissolved in alcohol, treated with hydrochloric acid in ethanol to form the title compound in hydrochloride form, m.p. 290°-292° (decomp.).

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. additionthe residual oil is treated with 30 ml ethanol
  3. temperatureto reflux over 30 minutes
  4. customthe hydrobromide of the title compound crystallizes out
  5. filtrationThe salt is then filtered off
  6. washwashed with a little alcohol
  7. custompartitioned between dichloromethane and aqueous ammonia
  8. customto form the free base
  9. customThe organic phase is separated off
  10. washwashed with water
  11. dry with materialdried over sodium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. dissolutionThe oily residue is dissolved in alcohol
  15. additiontreated with hydrochloric acid in ethanol

Sources & evidence

ORD record
ord-fb7a579a8ab14cedae819974f2f2fb4c
Source dataset
uspto-grants-1984_10
Patent number
US04478750

Reaction notes

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