Toluene → HCID 13067133, compound

HRID 1388626Notes

Reaction equation

HRID 1388626 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. stirringstirred for 3 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 (25 g, silica gel; eluent 4:1 methylene chloride:ether)
  8. customgave an off-white solid, mp 130°-131°

Sources & evidence

ORD record
ord-8ecb7ca79a4e482d8ed98eac44c1553e
Source dataset
uspto-grants-1984_02
Patent number
US04431823

Reaction notes

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