Hydrochloric Acid → HCID 13067132, compound

HRID 223499Notes

Reaction equation

HRID 223499 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6]3[C:7](=[CH:18][NH:19][CH:20]=3)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1.CC(C)([O-])C.[K+].[CH3:29][N:30]([CH2:32][CH2:33][CH2:34][Cl:35])[CH3:31].Cl>CN(C)C=O.O.C1(C)C=CC=CC=1>[ClH:1].[ClH:35].[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6]3[C:7](=[CH:18][N:19]([CH2:34][CH2:33][CH2:32][N:30]([CH3:31])[CH3:29])[CH:20]=3)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 23665647Potassium tert-butoxideHCID 136045442HCID 136045442, compound

Product 1

HCID 13067132HCID 13067132, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

In one portion 1.5 g (4.8 mmol) of 8-chloro-6-(2-fluorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine was added to a solution of 0.6 g (5.3 mmol) of potassium t-butoxide in 25 ml of dimethylformamide which was cooled to 0°. After stirring for 15 min, 5.2 ml (10.4 mmol) of a 2 M toluene solution of dimethylaminopropyl chloride was added. The mixture was warmed to room temperature and stirred for 4 hr. The mixture was diluted with water and extracted with methylene chloride. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate and concentrated at reduced pressure. Purification of the residue by column chromatography (silica gel, 25 g; eluents, 4:1 ration of methylene chloride:ether followed by 1:2:7 ratio of methanol:ether:methylene chloride) gave a colorless oil. The oil was dissolved in an excess of methanolic hydrogen chloride and the solution was concentrated at reduced pressure. Crystallization of the residue from a mixture of isopropanol and ether gave an orange solid, mp 258°-260°.

Workup

  1. temperaturewas cooled to 0°
  2. stirringstirred for 4 hr
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customPurification of the residue by column chromatography (silica gel, 25 g; eluents, 4:1 ration of methylene chloride:ether followed by 1:2:7 ratio of methanol:ether:methylene chloride)
  8. customgave a colorless oil
  9. concentrationthe solution was concentrated at reduced pressure
  10. customCrystallization of the residue
  11. additionfrom a mixture of isopropanol and ether
  12. customgave an orange solid, mp 258°-260°

Sources & evidence

ORD record
ord-ea6bb4f21b76400ea05e7fe3e43c2ce2
Source dataset
uspto-grants-1982_10
Patent number
US04354973

Reaction notes

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