Water → HCID 13067109, compound

HRID 2296277Notes

Reaction equation

HRID 2296277 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.[CH3:23]C(C)([O-])C.[K+].CI.O>CN(C)C=O>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6]3[C:7](=[CH:18][N:19]([CH3:23])[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

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 136045442HCID 136045442, compound

Product 1

HCID 13067109HCID 13067109, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In one portion, 0.7 g (2.2 mmole) of 8-chloro-6-(2-fluorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine was added to a solution of 0.3 g (2.6 mmole) of potassium t-butoxide in 30 ml of dry dimethylformamide which was cooled to 0° C. After stirring for 15 minutes 1.0 ml (16 mmole) of methyl iodide was added, and the mixture was allowed to warm to room temperature. Water was added, and the mixture was extracted with methylene chloride. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to give a yellow oil. Purification by column chromatography (silica gel, 20 g; eluent 5% ether in methylene chloride) gave a tan solid (mp 142°-144° C.). Recrystallization from a mixture of ether and petroleum ether gave cream colored prisms, mp 144°-146° C.

Workup

  1. additionwas added
  2. temperatureto warm to room temperature
  3. extractionthe mixture was extracted 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. customto give a yellow oil
  8. customPurification by column chromatography (silica gel, 20 g; eluent 5% ether in methylene chloride)

Sources & evidence

ORD record
ord-2ac1cce6502f4f82857f1f683c9c43c5
Source dataset
uspto-grants-1984_01
Patent number
US04428878

Reaction notes

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