4-Nitrobenzoyl chloride → 4-(p-Nitrobenzoyl)-4-azatricyclo[4.3.1.13,8]undecane

HRID 637606Notes

Reaction equation

HRID 637606 reaction equation
[CH:1]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:3]([NH:4][CH2:5]3)[CH2:2]1)[CH2:9]2.[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13]>C(O)C>[N+:12]([C:15]1[CH:16]=[CH:17][C:18]([C:19]([N:4]2[CH2:5][CH:6]3[CH2:11][CH:1]4[CH2:9][CH:8]([CH2:10][CH:3]2[CH2:2]4)[CH2:7]3)=[O:20])=[CH:22][CH:23]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 322724-Azatricyclo[4.3.1.13,8]undecane

Product 1

HCID 135603134-(p-Nitrobenzoyl)-4-azatricyclo[4.3.1.13,8]undecaneYield 83.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-azatricyclo[4.3.1.13,8 ]undecane (0.75 gram, 5 mmol) from Step B, and p-nitrobenzoyl chloride (0.93 gram, 5 mmol) in 40 ml anhydrous ethanol was refluxed for 4.5 hours. Following workup and recrystallization from isopropanol, 1.25 gram of compound 4b were obtained as white crystals (melting point 150° C.).

Workup

  1. temperaturewas refluxed for 4.5 hours
  2. customworkup and recrystallization from isopropanol

Sources & evidence

ORD record
ord-469ea42582a14c18b6b59d96b814d1ea
Source dataset
uspto-grants-1985_12
Patent number
US04557865

Reaction notes

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