Water → HCID 15916790, compound

HRID 354671Notes

Reaction equation

HRID 354671 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH:17][CH2:18][CH2:19][CH2:20][OH:21])[C:15]#[N:16])=[CH:10][CH:9]=1.O.[OH-].[Na+]>CCOCC.O1CCCC1>[NH2:16][CH2:15][CH:14]([NH:17][CH2:18][CH2:19][CH2:20][OH:21])[C:11]1[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15916789HCID 15916789, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15916790HCID 15916790, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Prepare a suspension of lithium aluminum hydride in 1.0 liter of cold (-10° C.) ethyl ether with stirring. Add to the suspension a solution of 50 g of 4-fluoro-α-[(3-hydroxypropyl)amino]benzeneacetonitrile in 500 ml of ether and 100 ml of tetrahydrofuran under nitrogen. Stir the reaction mixture for five (5) hours at 0° C. then overnight at room temperature. Cool the reaction mixture to 0° C. and treat dropwise with 38 ml of water followed by 38 ml of 15% sodium hydroxide solution and 70 ml of water. Stir the reaction mixture for one-half hour, filter and concentrate to a solid. Extract the filter cake with methylene chloride several times and concentrate the filtrate to a residue. Crystallize the residues from isopropyl ether to obtain thereby the title product melting 110°-112° C.

Workup

  1. customPrepare
  2. customovernight
  3. customat room temperature
  4. stirringStir the reaction mixture for one-half hour
  5. filtrationfilter
  6. concentrationconcentrate to a solid
  7. extractionExtract the filter cake with methylene chloride several times
  8. concentrationconcentrate the filtrate to a residue
  9. customCrystallize the residues from isopropyl ether
  10. customto obtain

Sources & evidence

ORD record
ord-a6a8a26dbedd41e19dc6380461c7e51d
Source dataset
uspto-grants-1983_03
Patent number
US04376769

Reaction notes

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