Phthalimide → 2-{4-[(Oxan-2-yl)oxy]nonyl}-1H-isoindole-1,3(2H)-dione

HRID 372510Notes

Reaction equation

HRID 372510 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.Cl[CH2:13][CH2:14][CH2:15][CH:16]([O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CN(C)C=O>[O:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]1[O:22][CH:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14][CH2:13][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

4

Reactant 2

HCID 6809PhthalimideHCID 203276861-Chloro-4-(2-tetrahydropyranyloxy)nonane

Product 1

HCID 203276592-{4-[(Oxan-2-yl)oxy]nonyl}-1H-isoindole-1,3(2H)-dioneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

Sodium hydride (53%) (1.5 g. excess) is washed with benzene three times by decantation, then dimethyl formamide (100 ml.) is added. To this stirred suspension is added a solution of phthalimide (4.3 g., 0.03 mole) in dimethyl formamide (50 ml.) at such a rate as to keep the temperature below 35° C. A clear solution is obtained and to it is added 1-chloro-4-(2-tetrahydropyranyloxy)nonane (7.8 g. 0.03 mole) and the resulting solution is stirred and heated at 95° C. for 20 hours. The reaction is then concentrated to one-half its volume in vacuo, poured into ice water (200 ml.) and extracted with ether (2 × 150 ml.). The ether is washed with 5% sodium hydroxide (2 × 50 ml.), saturated sodium chloride solution (2 × 50 ml.), then dried over sodium sulfate. Evaporation of the ether affords 4.5 g. (45% yield) of N-[4-(2-tetrahydropyranyloxy)nonyl]phthalimide melting 59°- 61° C. After crystallization from cyclohexane the product melts at 62°-63° C. Anal. Calcd. for C22H31NO4 : C, 70.75; H, 8.36; N, 3.75 Found: C, 71.03; H, 8.28; N, 3.81

Workup

  1. washSodium hydride (53%) (1.5 g. excess) is washed with benzene three times by decantation
  2. additiondimethyl formamide (100 ml.) is added
  3. customthe temperature below 35° C
  4. customA clear solution is obtained and to it
  5. concentrationThe reaction is then concentrated to one-half its volume in vacuo
  6. additionpoured into ice water (200 ml.)
  7. extractionextracted with ether (2 × 150 ml.)
  8. washThe ether is washed with 5% sodium hydroxide (2 × 50 ml.), saturated sodium chloride solution (2 × 50 ml.)
  9. dry with materialdried over sodium sulfate
  10. customEvaporation of the ether
  11. customaffords 4.5 g

Sources & evidence

ORD record
ord-9900a322a9294d9f80de872587879d45
Source dataset
uspto-grants-1978_05
Patent number
US04091107

Reaction notes

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