Aluminium lithium hydride → N-(1-benzyl-4-piperidinyl)-2-hydroxymethyl-3-fluoroaniline

HRID 266841Notes

Reaction equation

HRID 266841 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:22]=2[C:23](O)=[O:24])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH2:7]([N:14]1[CH2:15][CH2:16][CH:17]([NH:20][C:21]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:22]=2[CH2:23][OH:24])[CH2:18][CH2:19]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 540167532-(1-Benzyl-4-piperidinylamino)-6-fluorobenzoic acid

Product 1

HCID 19031041N-(1-benzyl-4-piperidinyl)-2-hydroxymethyl-3-fluoroanilineYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium aluminium hydride (0.9 g) in anhydrous tetrahydrofuran (160 ml) is added 2-(1-benzyl-4-piperidinylamino)-6-fluorobenzoic acid (8.0 g) and the mixture is refluxed for 1 hour. After cooling, the reaction solution is poured into ice-water and then extracted with dichloromethane. The solvent is concentrated and to the resulting residue is added diethyl ether/n-hexane. The precipitated crystal is collected by filtration to give N-(1-benzyl-4-piperidinyl)-2-hydroxymethyl-3-fluoroaniline (4.6 g) as light yellow powders, m.p.: 167°-170° C.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane
  4. concentrationThe solvent is concentrated and to the resulting residue
  5. additionis added diethyl ether/n-hexane
  6. filtrationThe precipitated crystal is collected by filtration

Sources & evidence

ORD record
ord-c6535e91507f4f96867496832714eab8
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

Loading…