Cyclohexylamine → HCID 178478536, compound

HRID 1660502Notes

Reaction equation

HRID 1660502 reaction equation
[C:1]1([C:7]2[NH:12][CH2:11][CH:10]([CH2:13][Cl:14])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[ClH:14].[ClH:14].[C:1]1([C:7]2[NH:12][CH2:11][CH:10]([CH2:13][NH:21][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 7965CyclohexylamineHCID 178478441HCID 178478441, compound

Product 1

HCID 178478536HCID 178478536, compound

Procedure

To 5.0 g. of 3-phenyl-6-chloromethyl-5,6-dihydro-4H-1,2,4-oxadiazine (Chem. Ber. 108, 1911 (1975) 37 ml. of cyclohexyl amine are added. The reaction mixture is then refluxed for 10 hours. The excess of cyclohexyl amine is evaporated in vacuo and to the evaporation residue 100 ml. of ethyl acetate are added. The mixture is brought to the boil and the insoluble substances are filtered off while hot. The mother liquor is evaporated in vacuo, the residue is dissolved in isopropanol and the solution is acidified by introducing hydrogen chloride gas. 4.0 g. of 3-phenyl-6-cyclohexylaminomethyl-5,6-dihydro-4H-1,2,4-oxadiazine dihydrochloride are obtained, melting at 240° to 244° C. (after recrystallization from isopropanol).

Workup

  1. temperatureThe reaction mixture is then refluxed for 10 hours
  2. customThe excess of cyclohexyl amine is evaporated in vacuo and to the evaporation residue 100 ml
  3. additionof ethyl acetate are added
  4. filtrationthe insoluble substances are filtered off while hot
  5. customThe mother liquor is evaporated in vacuo
  6. dissolutionthe residue is dissolved in isopropanol
  7. additionby introducing hydrogen chloride gas

Sources & evidence

ORD record
ord-b754945b0af94898865b3a4da717ff38
Source dataset
uspto-grants-1981_12
Patent number
US04308270

Reaction notes

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