Ammonium Hydroxide → HCID 13225521, compound

HRID 464538Notes

Reaction equation

HRID 464538 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][N:7]=[C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:9]3[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:10]=3[C:11]=2[N:12]=1.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[OH-].[NH4+]>CN(C)C=O>[ClH:1].[Cl:17][C:15]1[CH:14]=[CH:13][C:10]2[C:11]3[N:12]=[C:2]([N:29]4[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]4)[N:3]=[CH:4][C:5]=3[CH2:6][N:7]=[C:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:9]=2[CH:16]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 531671-MethylpiperazineHCID 13225515HCID 13225515, compound

Product 1

HCID 13225521HCID 13225521, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.0 g (0.00838 mol) of 2,9-dichloro-7-(2-fluorophenyl)-5H-pyrimido[5,4-d][2]benzazepine in 8 ml of N,N-dimethylformamide was added 2 g (0.02 mol) of N-methylpiperazine. After 20 hr ice water (40 ml) was added to the reaction which was then filtered. The solid was partitioned between 50 ml of dichloromethane and 50 ml of 1N hydrochloride acid, and the pH was adjusted to 1-2 with ammonium hydroxide. The resulting precipitate was filtered and recrystallized twice from methanol to give white prisms, mp 187°-194° C. The acid layer was made basic with ammonium hydroxide, and extracted with 100 ml of dichloromethane which was dried and evaporated. The oil was acidified with 1N hydrochloric acid, adjusted to pH 1-2 with ammonium hydroxide, cooled and filtered. The precipitate was recrystallized from methanol to give a further crop of the product.

Workup

  1. filtrationwas then filtered
  2. customThe solid was partitioned between 50 ml of dichloromethane and 50 ml of 1N hydrochloride acid
  3. filtrationThe resulting precipitate was filtered
  4. customrecrystallized twice from methanol
  5. customto give white prisms, mp 187°-194° C
  6. extractionextracted with 100 ml of dichloromethane which
  7. customwas dried
  8. customevaporated
  9. temperaturecooled
  10. filtrationfiltered
  11. customThe precipitate was recrystallized from methanol
  12. customto give a further crop of the product

Sources & evidence

ORD record
ord-7af6cbf5486045828b5a4676a3d14220
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

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