HCID 13036367, compound → HCID 15917705, compound

HRID 128081Notes

Reaction equation

HRID 128081 reaction equation
I.[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[NH:17])[NH2:16])[CH2:11][CH2:10]1)=[O:8].C(N1CCN(C2N=[C:34]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=[C:35]3N=2)CC1)(=O)C1C=CC=CC=1.C1(CN2CCN(C3N=C4C=CC=CC=C4N=3)CC2)C=CC=CC=1.C1(N2CCN(C3N=C4C=CC=CC=C4N=3)CC2)C=CC=CC=1.C(N1CCN(C2N=C3C=CC=CC=C3N=2)CC1)=O>C(OCC)(=O)C.CO>[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:16]=[C:34]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=[C:35]3[N:17]=2)[CH2:11][CH2:10]1)=[O:8]

Participants

8

Reactant 5

HCID 13036367HCID 13036367, compoundHCID 15917704HCID 15917704, compoundHCID 20284334Cycloheptimidazole, 2-[4-(phenylmethyl)-1-piperazinyl]-HCID 20284373HCID 20284373, compoundHCID 20284377HCID 20284377, compound

Product 1

HCID 15917705HCID 15917705, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent4×

Procedure

In the same manner but replacing 4-(2-furanylcarbonyl)-1-piperazinecarboximidamide hydroiodide with an equivalent amount of another compound of formula III, described in Example 12, the following compounds of formula I were obtained, respectively: 2-(4-benzoyl-1-piperazinyl)cycloheptimidazole: (I: R1 is benzoyl) mp 148°-149° C.(ethyl acetate); ir(mull)1623 cm-1 and uv max(MeOH) 289(ε30,340), 263(ε29,700) and 239 nm(ε7,950); 2-[4-(phenylmethyl)-1-piperazinyl]-cycloheptimidazole: (I: R1 is phenylmethyl) mp 97°-99° C.(ethyl acetate); ir(CHCl3) 3660, 3330, 1600, 1565, 1525, 1495 and 697 cm-1 ; uv max (MeOH) 295 (ε6,750), 251(ε26,440) and 238 nm(ε25,860); nmr (CDCl3)δ2.6(4H,t), 3.57(2H,s), 4.05(4H,t) and 7.35-8.15(10H,m) and Anal. Calcd for C19H20N4 : C, 74.90% H, 6.65% N, 18.45% and Found: C, 74.63% H, 6.60% N, 77.65%; 2-(4-phenyl-1-piperazinyl)cycloheptimidazole: (I: R1 is phenyl) mp 210°-212° C. (ethyl acetate); ir(mull) 1595, 1570, 1530 and 1503 cm-1 ; uv max (MeOH) 288(δ7,960), 260(ε34,040) and 241 nm(ε29,530); nmr(CDCl3)δ3.35(4H,t), 4.23(4h,t) and 7.5(10H,m) and Anal. Calcd. for C18H18N4O: C, 74.46% H, 6.25%, N, 19.29% and Found C, 74.12% H, 6.07% N, 19.16%; and 2-(4-formyl-1-piperazinyl)cycloheptimidazole: (I: R1 is formyl) mp 165°-167° C. (ethyl acetate); ir(mull) 1670 cm-1 ; nmr(CDCl3)δ 3.9(8H,m) and 7.9(6H,m) and Anal. Calcd for C13H14N4O: C, 64.43% H, 5.82% N, 23.12% and Found: C, 64.44% H, 5.80% N, 22.66%.

Workup

  1. customthe following compounds of formula I were obtained

Sources & evidence

ORD record
ord-da81c5e7e268496f8912f6d3527639ea
Source dataset
uspto-grants-1981_03
Patent number
US04258188

Reaction notes

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