2-Octylcyclopropane-1-carbonyl chloride → HCID 178442565, compound

HRID 34750Notes

Reaction equation

HRID 34750 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH2:10])=[NH:9].[CH2:11]([CH:19]1[CH2:21][CH:20]1[C:22](Cl)=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>N1C=CC=CC=1>[CH2:11]([CH:19]1[CH2:21][CH:20]1[C:22]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH2:10])=[NH:9])=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 212989522-Octylcyclopropane-1-carbonyl chlorideHCID 178512824HCID 178512824, compound

Product 1

HCID 178442565HCID 178442565, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 350 mg. of 1-amino-5-guanidinopentane suspended in 70 ml. of dry pyridine was added 700 mg. of 2-(n-octyl)cyclopropanecarbonyl chloride. This mixture was stirred at room temperature for 2 days, after which the solid was filtered and the filtrate concentrated to a brown oil (1.19 g.). The entire bulk of this oil was chromatographed on silica gel eluting with MeOH:CHCl3 (2:3) and collecting 10 ml. fractions. Fractions 20-40 gave 28.8 mg. of desired products. Mass spectrometry (EI): M+ m/e 324 for C18H36N4O.

Workup

  1. filtrationafter which the solid was filtered
  2. concentrationthe filtrate concentrated to a brown oil (1.19 g.)
  3. customThe entire bulk of this oil was chromatographed on silica gel eluting with MeOH:CHCl3 (2:3)
  4. customcollecting 10 ml
  5. customFractions 20-40 gave 28.8 mg

Sources & evidence

ORD record
ord-b48e7027f46a4931bbb9921abd428a80
Source dataset
uspto-grants-1988_08
Patent number
US04762949

Reaction notes

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