4-Pyridineethanamine → HCID 178526948, compound

HRID 1722021Notes

Reaction equation

HRID 1722021 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([C:11]2[CH:21]=[CH:20][C:14]([O:15][CH2:16][CH:17]3[O:19][CH2:18]3)=[CH:13][CH:12]=2)[NH:9][CH:10]=1.[NH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1>C(O)(C)C>[OH2:15].[N:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH2:23][NH:22][CH2:18][CH:17]([OH:19])[CH2:16][O:15][C:14]2[CH:20]=[CH:21][C:11]([C:8]3[NH:9][CH:10]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[N:7]=3)=[CH:12][CH:13]=2)=[CH:26][CH:27]=1.[N:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH2:23][NH:22][CH2:18][CH:17]([OH:19])[CH2:16][O:15][C:14]2[CH:20]=[CH:21][C:11]([C:8]3[NH:9][CH:10]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[N:7]=3)=[CH:12][CH:13]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 832754-PyridineethanamineHCID 178420847HCID 178420847, compound

Product 1

HCID 178526948HCID 178526948, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-{p-[4-(2-thienyl)-2-imidazolyl]phenoxy}-1,2-epoxypropane (5.0 g, 0.017 m) and 4-(2-aminoethyl)pyridine (3.18 g, 0.026 m) in isopropanol (90 ml) was stirred at 70° C. for 23 hours. The solvent was evaporated under reduced pressure and the residue chromatographed on silica gel and eluted with 5% MeOH-CHCl3 saturated with NH3, and then rechromatographed eluting with 10% MeOH-CHCl3 saturated with NH3. Compound 78 was isolated as an amorphous solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue chromatographed on silica gel
  3. washeluted with 5% MeOH-CHCl3 saturated with NH3
  4. customrechromatographed
  5. washeluting with 10% MeOH-CHCl3 saturated with NH3

Sources & evidence

ORD record
ord-7562db348ff84f628a1828f499cafa4c
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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