Ammonia → HCID 21411749, compound

HRID 2071650Notes

Reaction equation

HRID 2071650 reaction equation
N.[Na].[N:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:15][CH3:16])[CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1.C1[O:19]C1.[Cl-].[NH4+]>C(OCC)C>[N:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])[CH2:15][CH2:16][OH:19])=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 222Ammonia2×HCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 21411779HCID 21411779, compound

Product 1

HCID 21411749HCID 21411749, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To stirred liquid ammonia (2 liters) was added ferric nitrate (0.1 gm) followed by sodium metal (8.0 gms) in 1 gram pieces over a period of 20 minutes. To the resulting solution was added 3-(4-pyridyl)-1-dimethylaminopentane (49 gms) over a period of 3 minutes and a deep yellow colour was allowed to develop over a period of 2 hours. Liquid ethylene oxide (14.6 gms) was then added and the mixture was stirred for a further 3 hours. Solid ammonium chloride (20 gms) was then added in small portions, followed by diethyl ether (1 liter). The ammonia was allowed to evaporate overnight and the residual mixture was filtered. The solvent was evaporated from the filtrate and the residual oil was distilled to yield 3-(4-pyridyl)-5-dimethylamino pentan-1-ol (32 gms, 46% conversion) b.p. 140°-146° C/0.5 mm Hg (m.p. 26° C).

Workup

  1. customto evaporate overnight
  2. filtrationthe residual mixture was filtered
  3. customThe solvent was evaporated from the filtrate
  4. distillationthe residual oil was distilled

Sources & evidence

ORD record
ord-fd669db9b1cb41479197a11bea7b9c5d
Source dataset
uspto-grants-1977_09
Patent number
US04048180

Reaction notes

Loading…