1,3-Propanediol → HCID 178520883, compound

HRID 847844Notes

Reaction equation

HRID 847844 reaction equation
[Na].Cl.Cl[CH2:4][C:5]1[N:6]=[CH:7][NH:8][CH:9]=1.[CH2:10]([OH:14])[CH2:11][CH2:12][OH:13]>>[OH:13][CH2:12][CH2:11][CH2:10][O:14][CH2:4][C:5]1[N:6]=[CH:7][NH:8][CH:9]=1

Participants

4

Reactant 3

HCID 104421,3-PropanediolHCID 5360545SodiumHCID 178478565HCID 178478565, compound

Product 1

HCID 178520883HCID 178520883, compound

Procedure

Sodium (13.5 g.) was added over 3 hours to propane-1,3-diol (450 ml.) under nitrogen at 70° with stirring. This solution was added over 20 minutes to a stirred solution of 4-chloromethylimidazole hydrochloride (50.0 g.) under nitrogen at 40°-60°. Subsequent heating at 60°-65° for 3 hours followed by overnight cooling, filtration and concentration gave 4-(3-hydroxypropoxy)methylimidazole. Subsequent reaction with thionyl chloride gave 4-(3-chloropropoxy)methylimidazole hydrochloride (38.3 g.). (ii) The reaction of this chloride (36.2 g.) with sodium azide (22.4 g.) in dry dimethylformamide at 95° for 3 hours followed by `dry-column` chromatography on aluminium with ethanol as eluant gave 4-(3-azidopropoxy)methylimidazole which was further purified by the same method using chloroform as eluant. The azide (2.95 g.) in ethanol (200 ml.) was hydrogenated over platinum oxide catalyst to give 4-(3-aminopropoxy)methylimidazole (2.42 g.).

Workup

  1. temperatureSubsequent heating at 60°-65° for 3 hours
  2. temperaturecooling
  3. filtrationfiltration and concentration

Sources & evidence

ORD record
ord-e16141bfa3f24178a47968f0b5792136
Source dataset
uspto-grants-1981_10
Patent number
US04293697

Reaction notes

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