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Ammonium Hydroxide → Seganserin

HRID 1980150
Notes
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Reaction equation

HRID 1980150 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[C:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[C:24](=[O:25])[N:23]4[CH:26]=[CH:27][CH:28]=[CH:29][C:22]4=[N:21][C:20]=3[CH3:30])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[OH-].[NH4+]>O>[F:37][C:34]1[CH:35]=[CH:36][C:31]([C:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)=[C:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]3[C:24](=[O:25])[N:23]4[CH:26]=[CH:27][CH:28]=[CH:29][C:22]4=[N:21][C:20]=3[CH3:30])[CH2:15][CH2:16]2)=[CH:32][CH:33]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 159037R-56413

Product 1

HCID 71767Seganserin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 Parts of 3-[2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one dihydrochloride were dissolved in water and the base was liberated with ammonium hydroxide. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was stirred in a dilute ammonium hydroxide solution. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane. The product was filtered off and dried, yielding 2.2 parts of 3-[2-[4-[bis(4-fluorophenyl)methylene]-1-piperidinyl]ethyl]-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; mp. 108.7° C. (compound 156).

Workup

  1. extractionThe product was extracted with dichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. extractionThe product was extracted with dichloromethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-021ad052611a497abeb681eef3bb627c
Source dataset
uspto-grants-1984_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04485107

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes