Phthalimide → N-[3-(4-Pyridyl)propyl]phthalimide

HRID 2186042Notes

Reaction equation

HRID 2186042 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[N:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21]O)=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42]1(=[O:52])[NH:46][C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12>C1COCC1>[N:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][N:46]2[C:45](=[O:47])[C:44]3=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]3[C:42]2=[O:52])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 729234-PyridinepropanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 12015796N-[3-(4-Pyridyl)propyl]phthalimideYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl azodicarboxylate (4.4 g, 25.4 mmol) was dissolved in dry THF and added dropwise to a solution of 3-(4-pyridyl)propanol (3.18 g, 23.18 mmol), triphenylphosphine (12.3 g, 46.9 mmol) and phthalimide (3.6 g, 24.5 mmol) in dry THF (50 mL). The mixture was stirred at RT for 3.5 h, concentrated and the residue taken up in ether and filtered. The filter cake was taken up in hexane/ethyl acetate/chloroform (40:30:30) and flash chromatographed (silica gel, 30:35:35 hexane:ethyl acetate:chloroform) (3 L) to yield the title compound (3.3 g, 54%). 1H NMR (90 MHz, CDCl3) δ8.44 (m, 2H), 7.71 (m, 4H), 7.13 (d, 2H), 3.70 (t, 2H), 2.65 (t, 2H), 2.05 (m, 2H)

Workup

  1. concentrationconcentrated
  2. filtrationfiltered
  3. customflash chromatographed (silica gel, 30:35:35 hexane:ethyl acetate:chloroform) (3 L)

Sources & evidence

ORD record
ord-b30c51dc8a8645e3b15fb3062a97dcaa
Source dataset
uspto-grants-2002_06
Patent number
US06403578B1

Reaction notes

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