Cyclopropylamine → HCID 13157369, compound

HRID 325356Notes

Reaction equation

HRID 325356 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]2[O:14][CH2:13]2)=[CH:8][CH:7]=1.[CH:17]1([NH2:20])[CH2:19][CH2:18]1>>[CH:17]1([NH:20][CH2:13][CH:12]([OH:14])[CH2:11][O:10][C:9]2[CH:15]=[CH:16][C:6]([C:2]3[NH:3][CH:4]=[CH:5][N:1]=3)=[CH:7][CH:8]=2)[CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 13157368HCID 13157368, compound

Product 1

HCID 13157369HCID 13157369, compound

Procedure

A mixture of 3-[p-(2-imidazolyl)phenoxy]-1,2-epoxypropane (4.95 g., 0.023 m.) in cyclopropylamine (50 ml.) is refluxed at 60° for 30 hours. The mixture is concentrated under reduced pressure and the residue is chromatographed on silica gel, eluting with 5-10% MeOH-CHCl3 saturated with NH3. The free base (IV) (1.21 g., 19%) is crystallized as the dihydrochloride salt from EtOH-MeOH-ether (m.p. 214°-5°).

Workup

  1. temperatureis refluxed at 60° for 30 hours
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customthe residue is chromatographed on silica gel
  4. washeluting with 5-10% MeOH-CHCl3 saturated with NH3
  5. customThe free base (IV) (1.21 g., 19%) is crystallized as the dihydrochloride salt from EtOH-MeOH-ether (m.p. 214°-5°)

Sources & evidence

ORD record
ord-8902a1962c3b45a9a260b974227ffde1
Source dataset
uspto-grants-1984_04
Patent number
US04440774

Reaction notes

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