Sodium hydride → 5-(2'-Aminoethyl)-3-chloro-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyridine

HRID 647974Notes

Reaction equation

HRID 647974 reaction equation
[H-].[Na+].[NH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([Cl:13])[C:9](Cl)=[N:10][CH:11]=1.[OH:14][CH2:15][CH:16]1[O:20]C(C2C=CC=CC=2)[N:18]([CH:27]([CH3:29])[CH3:28])[CH2:17]1>COCCOC>[NH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([Cl:13])[C:9]([O:14][CH2:15][CH:16]([OH:20])[CH2:17][NH:18][CH:27]([CH3:29])[CH3:28])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 125661982-Phenyl-3-isopropyl-5-hydroxymethyloxazolidineHCID 20483526HCID 20483526, compound

Product 1

HCID 204833965-(2'-Aminoethyl)-3-chloro-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyridine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

12 g of sodium hydride dispersion (55% strength) are added in portions to 44 g of 5-(2'-aminoethyl)-2,3-dichloro-pyridine and 55 g of 5-hydroxymethyl-3-isopropyl-2-phenyl-oxazolidine, dissolved in 500 ml of 1,2-dimethoxyethane, whilst cooling with ice at 0°-10° C. The reaction mixture is then stirred for 2 hours at room temperature and 16 hours under reflux. Working up gives crude 5-(2'-aminoethyl)-3-chloro-2-[3'-isopropyl-2'-phenyloxazolidinyl-(5')]-methoxy-pyridine, which is hydrolysed without further purification, analogously to Example (37), to give 5-(2'-aminoethyl)-3-chloro-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyridine (boiling point 165°-185° C./0.06 mm Hg).

Workup

  1. temperaturewhilst cooling with ice at 0°-10° C
  2. temperatureunder reflux
  3. customWorking up gives crude 5-(2'-aminoethyl)-3-chloro-2-[3'-isopropyl-2'-phenyloxazolidinyl-(5')]-methoxy-pyridine, which
  4. customis hydrolysed without further purification, analogously to Example (37)

Sources & evidence

ORD record
ord-ea0b06c38d4a4ff589133bfd1a5b2d32
Source dataset
uspto-grants-1983_10
Patent number
US04410530

Reaction notes

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