HCID 14556114, compound → 1334147-09-9

HRID 1606916Notes

Reaction equation

HRID 1606916 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 ethanol 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 ethanol
  4. customproduced a solid
  5. custommelting above 310° C

Sources & evidence

ORD record
ord-89d98d1cf16b46d484a5b682fc055afe
Source dataset
uspto-grants-1989_09
Patent number
US04863919

Reaction notes

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