Water → HCID 18175257, compound

HRID 395595Notes

Reaction equation

HRID 395595 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([CH2:12][C:13]2[CH:18]=[C:17]([NH:19][C:20](=O)[CH3:21])[CH:16]=[C:15]([CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:14]=2[OH:29])[CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[Na+]>O1CCCC1>[N:7]1([CH2:12][C:13]2[CH:18]=[C:17]([NH:19][CH2:20][CH3:21])[CH:16]=[C:15]([CH2:23][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[C:14]=2[OH:29])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 13362486HCID 13362486, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18175257HCID 18175257, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of lithium aluminum hydride (2.7 g) in tetrahydrofuran (25 ml) was added dropwise a solution of 2,6-bis(1-pyrrolidinomethyl)-4-acetamidophenol (5.6 g) in tetrahydrofuran (5 ml). The mixture was heated to reflux for 5 hours and was added dropwise water and aqueous 20% NaOH solution with cooling in an ice bath then was filtered by suction. The filtered cake was washed with tetrahydrofuran. The combined filtrate and washings were evaporated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (CH3COOEt:CH3OH: H4OH=5:1:0.1) to give 2,6-bis(1-pyrrolidinomethyl)-4-ethylaminophenol (3.9 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hours
  3. temperaturewith cooling in an ice bath
  4. filtrationthen was filtered by suction
  5. washThe filtered cake was washed with tetrahydrofuran
  6. customThe combined filtrate and washings were evaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by silica gel column chromatography (CH3COOEt:CH3OH: H4OH=5:1:0.1)

Sources & evidence

ORD record
ord-9d483b89dce14bbb8ea91e5cee233057
Source dataset
uspto-grants-2003_08
Patent number
US06605635B1

Reaction notes

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