Sodium Sulfate → N-(5-hydroxypentyl) heptylamine

HRID 486082Notes

Reaction equation

HRID 486082 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:14][C:15](=O)[CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[OH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 10262728Pentanamide, N-heptyl-5-hydroxy-HCID 21226445Aluminium lithium hydride

Product 1

HCID 10352800N-(5-hydroxypentyl) heptylamineYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Part B. To a solution of lithium aluminum hydride (6.7 g, 0.176 mol) in dry tetrahydrofuran (300 mL), a solution of N-heptyl-5-hydroxypentanamide (19.0 g, 0.088 mol) in dry tetrahydrofuran (100 mL) under a nitrogen atmosphere was added dropwise. The reaction mixture was heated to reflux for 18 hours, allowed to cool to room temperature and was poured slowly into a stirred mixture of 10% aqueous sodium sulfate (400 mL) and ice (200 mL). The resulting slurry was filtered through a bed of Celite® and the filtrate was extracted with ethyl acetate (2×500 mL). The combined organic extracts were washed with water and brine, then dried over magnesium sulfate and concentrated to give a viscous yellow oil. The product was crystallized from hexane to give N-(5-hydroxypentyl)-N-heptylamine (15.2 g, 0.075 mol) as a white powder, mp 47°-48°. 1H NMR (CDCl3) δ3.63 (t,2H,J=8.4 Hz), 2.63 (quartet,4H,J=8.3 Hz), 2.39 (bs,2H), 1.66-1.24 (m,16H), 0.91 (t,3H,J=6.6 Hz).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 hours
  3. filtrationThe resulting slurry was filtered through a bed of Celite®
  4. extractionthe filtrate was extracted with ethyl acetate (2×500 mL)
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give a viscous yellow oil
  9. customThe product was crystallized from hexane

Sources & evidence

ORD record
ord-9a6a4c0989224c5c8c51224719476c2f
Source dataset
uspto-grants-1994_03
Patent number
US05290801

Reaction notes

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