Hexane → HCID 13754536, compound

HRID 1249577Notes

Reaction equation

HRID 1249577 reaction equation
[C:1]1([C:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15](=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].CCCCCC>C1(C)C=CC=CC=1>[C:31]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][CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[CH2:13][CH2:14]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 129491Ro 23-7637HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 13754536HCID 13754536, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared in a manner similar to that employed for the compound of Example 16 starting with 6.5 g of 4-(2,2-diphenylethenyl)-1-[1-oxo-9-(3-pyridinyl)nonyl]piperidine and 7.7 mL of a 3.5M solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene. The analytically pure base was obtained from hexane, mp 51°-53° C. Analysis Calculated for C33H42N2 : C. 84.93; H, 9.07; N, 6.00. Found: C, 85.20; H, 9.00; N, 6.05. Evaporation of the hexane filtrates provided 5.9 g of crude product, which was dissolved in 25 mL of hot methanol and treated with 1.47 g of fumaric acid. The methanol was removed by distillation while adding acetone and the resulting solids were recovered and recrystallized from methanol/acetone to give 6.7 g (85%) of pure fumarate salt of 3-[9-[4-(2,2-diphenylethenyl)-1-piperidinyl]nonyl]pyridine, mp 125°-127° C. Analysis Calculated for C33H42N2.C4H4O4 : C, 76.26; H, 7.96; N, 4.81. Found: C, 76.54; H, 7.92; N, 4.90.

Workup

  1. customEvaporation of the hexane filtrates
  2. customprovided 5.9 g of crude product, which

Sources & evidence

ORD record
ord-a3c0eebf36eb4b9d85bf8f5925b2652d
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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