1,2,3,4-Tetrahydro-1-naphthylamine → HCID 178512346, compound

HRID 543244Notes

Reaction equation

HRID 543244 reaction equation
[C:1]([NH:3][C:4](=[NH:12])OC1C=CC=CC=1)#[N:2].[CH:13]1([NH2:23])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1>CCOCC>[C:1]([NH:3][C:4](=[NH:12])[NH:23][CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)#[N:2]

Participants

4

Reactant 2

HCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 178512385HCID 178512385, compound

Product 1

HCID 178512346HCID 178512346, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
220 °C

Procedure

A 25 ml round bottom flask containing a mixture of 4.8 g of N-cyano-O-phenylisourea and 6 g of 1,2,3,4-tetrahydro-1-naphthylamine was placed in an oil bath preheated to 190° C. The bath temperature was raised to 220° C. over 20 minutes and maintained at 220° C. for 8 minutes. Upon cooling, the reaction mixture had a glass-like appearance. The product was isolated from the reaction mixture by thorough shaking of the reaction mixture with ether to remove the remaining starting materials and phenol, and decanting the ether solution which left the crude product as a white gummy residue. The crude product was further purified by chromatography on a column packed with silica gel and eluting initially with toluene then with toluene-ethyl acetate mixtures with gradual increase in the ethyl acetate content. This gave 4.61 g of the desired compound that had satisfactory data in spectroscopic analysis.

Workup

  1. additionA 25 ml round bottom flask containing
  2. customwas placed in an oil bath
  3. custompreheated to 190° C
  4. temperaturemaintained at 220° C. for 8 minutes
  5. temperatureUpon cooling
  6. customThe product was isolated from the reaction mixture
  7. customto remove the remaining starting materials and phenol
  8. customdecanting the ether solution which
  9. waitleft the crude product as a white gummy residue
  10. customThe crude product was further purified by chromatography on a column
  11. washeluting initially with toluene
  12. temperaturewith gradual increase in the ethyl acetate content

Sources & evidence

ORD record
ord-54a102000bd14107813e6ce40d112443
Source dataset
uspto-grants-1987_04
Patent number
US04661520

Reaction notes

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