HCID 20310626, compound → HCID 205959, compound

HRID 616607Notes

Reaction equation

HRID 616607 reaction equation
O[C:2]1([CH2:16][CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]2[CH:13]=[CH:14][CH:15]=[C:3]12>C(Cl)(Cl)Cl>[CH3:21][N:19]([CH3:20])[CH2:18][CH2:17][CH:16]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]2[CH:13]=[CH:14][CH:15]=[C:3]12

Participants

3

Reactant 1

HCID 20310626HCID 20310626, compound

Product 1

HCID 205959HCID 205959, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Hydrogen chloride gas is bubbled through a solution of 4.8 gm. (0.017 moles) of 11-hydroxy-11-(3-dimethylaminopropyl)-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepine in 70 ml. of chloroform at 0° C. for 5 minutes. The resulting dark mixture is stirred for an additional 5 minutes, and then washed with 6M NaOH to provide, after evaporation of the chloroform, 4.3 g. of 11-(3-dimethylaminopropylidene)-6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepine as an oil. It is converted to a crystalline oxalate by adding a solution of 266 mg. of the free base in 5 ml. of ethanol to a mixture of 90 mg. of oxalic acid and 2 ml. of ethanol and collecting the precipitate by filtration and air drying; m.p. 140°-165° C. (dec.).

Workup

  1. customHydrogen chloride gas is bubbled through a solution of 4.8 gm
  2. washwashed with 6M NaOH
  3. customto provide
  4. customafter evaporation of the chloroform, 4.3 g
  5. additionby adding a solution of 266 mg
  6. additionof ethanol to a mixture of 90 mg
  7. customof ethanol and collecting the precipitate
  8. filtrationby filtration and air
  9. customdrying

Sources & evidence

ORD record
ord-306a06df249344bbae8c1bb92401a9eb
Source dataset
uspto-grants-1978_02
Patent number
US04075225

Reaction notes

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