4-Pyridineethanamine → HCID 178526948, compound

HRID 235972Notes

Reaction equation

HRID 235972 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
  4. customCHCl3 saturated with NH3, and then rechromatographed
  5. washeluting with 10% MeOH

Sources & evidence

ORD record
ord-928bd5be60c446cfbcd4b293da22b027
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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