Maleate(2-) → HCID 13754524, compound

HRID 1249572Notes

Reaction equation

HRID 1249572 reaction equation
C1(C(C2C=CC=CC=2)C2CCN(CCCCC3C=NC=CC=3)CC2)C=CC=CC=1.C([O-])(=O)/C=C\C([O-])=O.[C:38]1([C:44]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)=[CH:45][CH:46]2[CH2:51][CH2:50][N:49]([C:52](=O)[CH2:53][CH2:54][CH2:55][C:56]3[CH:57]=[N:58][CH:59]=[CH:60][CH:61]=3)[CH2:48][CH2:47]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1(C)C=CC=CC=1>[C:63]1([C:44]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[CH:45][CH:46]2[CH2:47][CH2:48][N:49]([CH2:52][CH2:53][CH2:54][CH2:55][C:56]3[CH:57]=[N:58][CH:59]=[CH:60][CH:61]=3)[CH2:50][CH2:51]2)[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1

Participants

6

Reactant 4

HCID 5288227Maleate(2-)HCID 13754519HCID 13754519, compoundHCID 13754521HCID 13754521, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 13754524HCID 13754524, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared in a manner similar to that employed for 3-[4-[4-(diphenyl methyl)-1-piperidinyl]butyl]pyridine (1:1)-(Z)-2-butenedioate salt (Ex. 16) starting with 5.0 g of 4-(2,2-diphenylethenyl)-1-[1-oxo-4-(3-pyridinyl)butyl]piperidine and 7.2 mL of a 3.5M solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene. The analytically pure base was obtained from hexanne, mp 54°-56° C. Analysis Calculated for C28H32N2 : C, 84.80; H, 8.13; N, 7.06. Found: C. 84.61; H, 7.92; N, 7.05. Evaporation of the hexane filtrates provided 4.4 g of crude 3-[4-[4-(2,2-diphenylethenyl)-1-piperidinyl]butyl]pyridine, which was dissolved in 50 mL of hot ethanol and treated with 1.28 of fumaric acid. Dilution with 50 mL of ether provided 4.1 g (67%) of salt, mp 163°-165° C. Analysis Calculated for C28H32N2.C4H4O4 : C, 74.97; H, 7.08; N, 5.46. Found: C, 74.69; H, 7.07; N, 5.44.

Workup

  1. customThe title compound was prepared in a manner similar to
  2. customThe analytically pure base was obtained from hexanne, mp 54°-56° C
  3. customEvaporation of the hexane filtrates

Sources & evidence

ORD record
ord-98db3c26f2264333854a22e6673f35ec
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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