Fumaric Acid → 3-[8-[4-(2,2-diphenylethenyl)-1-piperidinyl]octyl]pyridine (E)-2-butenedioate salt

HRID 1249583Notes

Reaction equation

HRID 1249583 reaction equation
[C:1]1([C:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39]>C(O)C>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39].[C:29]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[CH2:13][CH2:14]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 137545063-[8-[4-(2,2-Diphenylethenyl)-1-piperidinyl]octyl]pyridine

Product 1

HCID 137545073-[8-[4-(2,2-diphenylethenyl)-1-piperidinyl]octyl]pyridine (E)-2-butenedioate saltYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2-L Erlenmeyer flask was charged with 205.5 g of 3-[8-[4-(2,2-diphenylethenyl)-1-piperidinyl]octyl]pyridine 420 mL of 2B ethanol, and 55.5 g (5% excess) of fumaric acid. The mixture was heated on a steam cone to solution and filtered through Celite into a 12-L flask equipped with a mechanical stirrer. The filter cake was washed with an additional 420 mL of warm 2B ethanol. The stirred filtrate was diluted rapidly with 5.10 L of acetone. Crystallization began within a few minutes. The suspension was cooled in an ice-acetone bath for 1.0 hour and filtered. The solid was washed with 2×1.0 L=2.0 L of cold acetone and dried in a forced air oven at 75° to give 249.9 g (97% yield) of 3-[8-[4-(2,2-diphenylethenyl)-1-piperidinyl]octyl]pyridine (E)-2-butenedioate salt as a white solid, mp 126°-127°. Lc showed this material to be homogeneous.

Workup

  1. temperatureThe mixture was heated on a steam cone to solution
  2. filtrationfiltered through Celite into a 12-L flask
  3. customequipped with a mechanical stirrer
  4. washThe filter cake was washed with an additional 420 mL
  5. temperatureof warm 2B ethanol
  6. additionThe stirred filtrate was diluted rapidly with 5.10 L of acetone
  7. customCrystallization
  8. waitbegan within a few minutes
  9. temperatureThe suspension was cooled in an ice-acetone bath for 1.0 hour
  10. filtrationfiltered
  11. washThe solid was washed with 2×1.0 L=2.0 L of cold acetone
  12. customdried in a forced air oven at 75°

Sources & evidence

ORD record
ord-3eb09357a836423999e8d15aa7fe10c7
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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