Hydrochloric Acid → 1-Methyl-4-[9-bromo-11H-pyrrolo[2,1-b] [3]benzazepin-11-ylidene]piperidine

HRID 1701710Notes

Reaction equation

HRID 1701710 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2(O)[C:14]3[CH:15]=[C:16]([Br:19])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][N:10]3[CH:20]=[CH:21][CH:22]=[C:9]23)[CH2:4][CH2:3]1.Cl.C(#N)C>C(Cl)(Cl)Cl>[CH3:1][N:2]1[CH2:3][CH2:4][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([Br:19])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][N:10]3[CH:20]=[CH:21][CH:22]=[C:9]23)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 13141172HCID 13141172, compound

Product 1

HCID 131411821-Methyl-4-[9-bromo-11H-pyrrolo[2,1-b] [3]benzazepin-11-ylidene]piperidineYield 64.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-Methyl-4-(9-bromo-11-hydroxy-11H-pyrrolo[2,1-b][3]benzazepin-11-yl)piperidine (8.8 g) is dissolved in 500 ml of chloroform and the solution stirred in an ice bath while dry hydrogen chloride gas is bubbled in until the solution is acidic. The flask is then stoppered and the mixture stirred at room temperature for six hours following which the mixture is carefully basified with dilute aqueous sodium carbonate. The layers are separated, the aqueous extracted twice with chloroform and the combined chloroform washed with dilute sodium bicarbonate and with water. After drying over magnesium sulfate the chloroform is removed on a film evaporator to give a dark brown oil. Trituration with acetonitrile gives slightly impure 1-methyl-4-(9-bromo-11H-pyrrolo[2,1-b][3]benzazepin-11-ylidene)piperidine (5.4 g, 64%), m.p. 138°-142° C.

Workup

  1. customis bubbled in until the solution
  2. customThe layers are separated
  3. extractionthe aqueous extracted twice with chloroform
  4. washthe combined chloroform washed with dilute sodium bicarbonate and with water
  5. dry with materialAfter drying over magnesium sulfate the chloroform
  6. customis removed on a film evaporator
  7. customto give a dark brown oil

Sources & evidence

ORD record
ord-dba774d2854541e6825f3c38d482d361
Source dataset
uspto-grants-1980_03
Patent number
US04195091

Reaction notes

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