Octylamine → HCID 178443621, compound

HRID 838919Notes

Reaction equation

HRID 838919 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9](OCC)[CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.[CH2:15]([NH2:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:15]([NH:23][C:9](=[N:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:10][CH3:11])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 3

HCID 8143OctylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 20325318HCID 20325318, compound

Product 1

HCID 178443621HCID 178443621, compound

Procedure

Ethyl N-(3-chlorophenyl)propionimidate (1 part), n-octyl-amine (1 part), and a catalytic amount of p-toluenesulfonic acid monohydrate were charged to a flask fitted with a condenser and drying tube (CaSO4) and the mixture was refluxed for 15 hours, after which the flask was fitted with a 10 cm Vigreaux column and the ethanol that had formed (0.8 part) distilled off slowly (3 hours). The reaction mixture was then distilled at reduced pressure (0.15 mm Hg) to give N-n-octyl-N'-(3-chlorophenyl)propionamidine (0.7 part). The fraction boiling at 167.5° - 169° C. was collected and analyzed.

Workup

  1. customfitted with a condenser
  2. dry with materialdrying tube (CaSO4)
  3. temperaturethe mixture was refluxed for 15 hours
  4. customafter which the flask was fitted with a 10 cm Vigreaux column
  5. customthe ethanol that had formed (0.8 part)
  6. distillationdistilled off slowly (3 hours)
  7. distillationThe reaction mixture was then distilled at reduced pressure (0.15 mm Hg)

Sources & evidence

ORD record
ord-c4750c4ab4ef421a9a767c324459f34d
Source dataset
uspto-grants-1978_06
Patent number
US04093655

Reaction notes

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