Hexane → 2-(4-hydroxybutyl)-1H-Isoindole-1,3(2H)-dione

HRID 726712

Reaction equation

HRID 726712 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.C(N1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29])(OCC)=O.CCCCCC>O1CCCC1.C(OCC)(=O)C>[OH:6][CH2:5][CH2:4][CH2:3][CH2:2][N:1]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 258684-Amino-1-butanolHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 111175282-(4-hydroxybutyl)-1H-Isoindole-1,3(2H)-dioneYield 65.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-amino-1-butanol (5.616 g; 63 mmol) and triethylamine (12.3 ml; 88.2 mmol) in 130 ml tetrahydrofuran was treated with N-carbethoxyphthalimide (13.82 g; 63 mmol). The mixture was refluxed for 18 hours. TLC showed the formation of product (1:1 Ethyl acetate:Hexane Rf=0.3). The mixture was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with more ethyl acetate and the organic layers combined, dried (MgSO4), filtered, concentrated and the residue purified by flash chromatography; 200 g silica gel column using 2:3 ethyl acetate:Hexane followed by 1:1 to provide N-(4-hydroxybutyl)phthalimide as a white solid (9.108 g; 65.9% yield). 1H NMR (300 MHz, CDCl3): 1.426 (t, 2H, J=4.93 Hz); 1.597-1.663 (m, 2H); 1.738-1.813 (m, 2H); 3.668-3.768 (m, 4H); 7.715 (m, 2H); 7.838 (m, 2H).

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with more ethyl acetate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-a052719cc3ac4fa19cae3bb6b5e1681b
Source dataset
uspto-grants-1998_01
Patent number
US05710159

Linked notes

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