Hydrochloric Acid → 10-[4-(1H-Imidazol-1-yl)phenoxy]decaneamine

HRID 1417325Notes

Reaction equation

HRID 1417325 reaction equation
[N:1]1([C:6]2[CH:33]=[CH:32][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.NN.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.Cl>C(O)C>[N:1]1([C:6]2[CH:33]=[CH:32][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 675993582-[10-[4-(1H-Imidazol-1-yl)phenoxy]decyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 5441526510-[4-(1H-Imidazol-1-yl)phenoxy]decaneamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-[10-[4-(1H-imidazol-1-yl)phenoxy]decyl]-1H-isoindole-1,3(2H)-dione (Example 65) is converted to the free amino derivative by treatment with hydrazine in a refluxing ethanol solution. A portion is converted to its dihydrochloride salt by treatment with concentrated hydrochloric acid in ethanol to give the desired compound, m.p. 190°-192° C. The free base is obtained by treatment with excess 10N NaOH.

Sources & evidence

ORD record
ord-53d2697f111d4693869bdde0ea7ae1b4
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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