Ethylene Oxide → HCID 21411747, compound

HRID 2071656Notes

Reaction equation

HRID 2071656 reaction equation
[Na].[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.[CH2:12]1[O:14][CH2:13]1.[Cl-].[NH4+]>N>[N:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH2:13][OH:14])[CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 143474663-(Pyridin-4-yl)propan-1-amine

Product 1

HCID 21411747HCID 21411747, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To stirred liquid ammonia (300 mls) was added ferric nitrate (50 mgs) followed by sodium metal (4.5 gms). The mixture was allowed to stand for 30 minutes and then 3-(4-pyridyl)-1-amino propane (13.5 gms) was added. A deep yellow colour was allowed to develop over 1 hour and ethylene oxide (5.0 gms) was then added. The mixture was stirred for a further 2 hours after which time solid ammonium chloride (12 gms) was added. The solvent was allowed to evaporate overnight and the residual solid was extracted into pyridine. Evaporation of the pyridine and crystallisation of the residue from benzene yielded 3-(4-pyridyl)-1-amino-5-hydroxy pentane (3.4 gms; 17%). Characterised by the following spectral data:

Workup

  1. waitto develop over 1 hour
  2. additionwas added
  3. customto evaporate overnight
  4. extractionthe residual solid was extracted into pyridine
  5. customEvaporation of the pyridine and crystallisation of the residue from benzene

Sources & evidence

ORD record
ord-c423362dd75a404a8f7a5e5817becbef
Source dataset
uspto-grants-1977_09
Patent number
US04048180

Reaction notes

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