Ammonia → HCID 21411780, compound

HRID 2071649Notes

Reaction equation

HRID 2071649 reaction equation
N.[K].[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.[CH2:17]1[O:19][CH2:18]1.[Cl-].[NH4+].C([O:24]CC)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][O:24][CH2:18][CH2:17][OH:19])=[CH:5][CH:4]=1

Participants

7

Reactant 6

HCID 222Ammonia2×HCID 3283Diethyl EtherHCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 5462222PotassiumHCID 21411779HCID 21411779, compound

Product 1

HCID 21411780HCID 21411780, compoundYield 40%

Procedure

To stirred liquid ammonia (2 liters) was added ferric nitrate (0.1 gm) followed by potassium metal (12 gms) in 1 gram pieces over a period of 20 minutes. To the resulting solution was added 3-(4-pyridyl)-1-dimethylamino pentane (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 (22 gms) was 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 then filtered. The solvent was evaporated from the filtrate and the residual oil was distilled to yield 6-(4-pyridyl)-8-dimethylamino-3-oxaoctan-1-ol (30 gms, 40% conversion of starting material fed) b.p. 140°-148° C/1 mm Hg.

Workup

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

Sources & evidence

ORD record
ord-f5c966859635470f8c15189a7877dd8f
Source dataset
uspto-grants-1977_09
Patent number
US04048180

Reaction notes

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