HCID 14556114, compound → 1334147-09-9

HRID 364633Notes

Reaction equation

HRID 364633 reaction equation
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([NH:10][C:11](=[O:21])[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[CH2:3]2.[H][H]>CO.[Pt]=O>[ClH:1].[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([NH:10][CH:4]2[CH:5]3[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]3)[CH2:3]2)=[O:21])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 14556114HCID 14556114, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 145561161334147-09-9

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of N-(1-azabicyclo[2.2.2]oct-3-yl)-4-nitrobenzamide hydrochloride (11.55 g., 0.037 mole) in 170 ml of 80% aqueous methanol was shaken in a hydrogen atmosphere with a platinum oxide catalyst on the Parr hydrogenator. The calculated volume of hydrogen was taken up in one hour. The catalyst was filtered off through Celite and the filtrate taken to dryness via rotary evaporator. Several recrystallizations of the colorless crystalline residue from 70% aqueous methanol produced a solid melting above 310° C. NMR, MS, and IR supported the proposed structure. Yield of title compound was 8.43 g. (81.2%).

Workup

  1. filtrationThe catalyst was filtered off through Celite
  2. customthe filtrate taken to dryness via rotary evaporator
  3. customSeveral recrystallizations of the colorless crystalline residue from 70% aqueous methanol
  4. customproduced a solid
  5. custommelting above 310° C

Sources & evidence

ORD record
ord-a579007dc6da42e29d32d96d5feb4ba0
Source dataset
uspto-grants-1986_08
Patent number
US04605652

Reaction notes

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