Water → HCID 13067107, compound

HRID 647620Notes

Reaction equation

HRID 647620 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:24](C)([O-])[CH3:25].[K+].C(Br)C=C.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]([CH2:25][CH:24]=[CH2:23])[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 7841Allyl bromideHCID 23665647Potassium tert-butoxideHCID 136045442HCID 136045442, compound

Product 1

HCID 13067107HCID 13067107, 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 dimethyl formamide which was cooled to 0° C. After stirring for 15 minutes, 1.0 ml (11 mmole) of allyl bromide 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 yellow oil. Crystallization from a mixture of ether and petroleum ether gave a tan solid (mp 100°-102° C.). Recrystallization from a mixture of ether and petroleum ether gave colorless prisms, mp 104°-106° C.

Workup

  1. temperatureto warm to room temperature
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe methylene chloride solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customto give a yellow oil
  7. customPurification by column chromatography (silica gel, 20 g; eluent 5% ether in methylene chloride)
  8. customgave a yellow oil
  9. customCrystallization
  10. additionfrom a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-34ef9b1daba34af4ae0e671e308e1bc8
Source dataset
uspto-grants-1983_10
Patent number
US04409390

Reaction notes

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