Cyclohexylamine → HCID 12777837, compound

HRID 224480Notes

Reaction equation

HRID 224480 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12]2)=[C:4]([NH2:17])[N:3]=1.[CH:18]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C>[CH:11]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([NH:24][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:3][C:4]=3[NH2:17])[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 127778182-chloro-9-(2-cyclohexenyl)-9H-adenine

Product 1

HCID 12777837HCID 12777837, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-chloro-9-(2-cyclohexenyl)-9H-adenine (300 mg., 1.2 mmole) and 1 ml. of cyclohexylamine in 3 ml. of ethanol is heated at 120°-125° C. for a period of 89 hrs. in a sealed tube and then evaporated in vacuo to give an oil. Purification of residual oil by column chromatography on silica gel affords 288 mg (77%) of 9-(2-cyclohexenyl)-2-cyclohexylamino-9H-adenine, m.p. 108°-111° C. IR (KBr): 3315, 3170, 2925, 2845, 1630, 1600, 1530, 1470, 1405 cm-1. UV: λmaxEtoH 224 nm(ε26,500), 259 nm(ε11,100), 291 nm(ε9,900). NMR(CDCl3): δ 0.9-2.3(16H,m), 3.75(1H,br.s), 4.95(1H,br.s), 5.4-6.2(2H,m), 7.42(1H,s).

Workup

  1. customin a sealed tube and then evaporated in vacuo
  2. customto give an oil
  3. customPurification of residual oil by column chromatography on silica gel

Sources & evidence

ORD record
ord-6e69f20f8b174904aead8cb818af686e
Source dataset
uspto-grants-1980_11
Patent number
US04232155

Reaction notes

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