Toluene → HCID 13067133, compound

HRID 2296330Notes

Reaction equation

HRID 2296330 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[Cl:17])[C:4]=2[CH:3]=1.CC(C)([O-])C.[K+].C1(C)C=CC=CC=1.[CH2:36]([N:38]([CH2:41][CH2:42]Cl)[CH2:39][CH3:40])[CH3:37]>CN(C)C=O.O>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6]3[C:7](=[CH:18][N:19]([CH2:37][CH2:36][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH:20]=3)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 13364Diethylaminoethyl chlorideHCID 23665647Potassium tert-butoxideHCID 135967503HCID 135967503, compound

Product 1

HCID 13067133HCID 13067133, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In one portion 2.1 g (6.4 mmol) of 8-chloro-6-(2-chlorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine was added to a solution of 0.8 g (7.0 mmol) of potassium t-butoxide in 35 ml of dimethyl formamide which was cooled to 0°. After stirring for 15 min 2.5 ml (7.5 mmol) of a 3 M toluene solution of diethylaminoethyl chloride was added. The mixture was warmed to room temperature and stirred for 3 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 (25 g, silica gel; eluent 4:1 methylene chloride:ether) gave an off-white solid, mp 130°-131°.

Workup

  1. temperaturewas cooled to 0°
  2. additionwas added
  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 (25 g, silica gel; eluent 4:1 methylene chloride:ether)
  8. customgave an off-white solid, mp 130°-131°

Sources & evidence

ORD record
ord-7ec88f35af2640ee8d04ea85a5596f43
Source dataset
uspto-grants-1984_01
Patent number
US04428879

Reaction notes

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