Ammonium Hydroxide → Seganserin

HRID 1380262Notes

Reaction equation

HRID 1380262 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

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 1590373-(2-{4-[Bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one--hydrogen chloride (1/2)

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 hyroxide 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-86e7ed1934a44dd6b60c657d6bfd6a04
Source dataset
uspto-grants-1986_04
Patent number
US04581171

Reaction notes

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