Water → HCID 20080138, compound

HRID 1654284Notes

Reaction equation

HRID 1654284 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([NH:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([OH:17])[CH3:16])[CH3:8].O.[OH-].[Na+]>C1COCC1>[CH2:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([OH:17])[CH3:16])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 20080118HCID 20080118, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20080138HCID 20080138, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension of LiAlH4 (2.65 g, 0.0697 mol) in THF (60 ml), under nitrogen, was cooled in an ice bath and treated during 20 minutes with a solution of the product from Step II (4.6 g, 0.0266 mol) in THF (60 ml). The mixture was warmed to ambient temperature during 30 minutes and then refluxed gently for 3.5 hours. It was again cooled in an ice bath and treated cautiously first with H2O (6 ml) and then with 2.5N NaOH (5.1 ml). This mixture was stirred at ambient temperature for 1 hour and filtered. The filtrate was concentrated and crystallized from hexane to give 2.63 g of ethyl(6-hydroxyheptyl)amine, mp 37°-38° C. The analytical sample had mp 39°-41° C. Anal. calc'd for C9H21NO: C, 67.87; H, 13.29; N, 8.80. Found: C, 67.69; H, 13.45; N, 8.81.

Workup

  1. temperatureunder nitrogen, was cooled in an ice bath
  2. temperaturerefluxed gently for 3.5 hours
  3. temperatureIt was again cooled in an ice bath
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customcrystallized from hexane

Sources & evidence

ORD record
ord-2381ca1d308f4ebe925751cdffb3e740
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

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