Phthalimide → N-[2-[1-(4-fluorobenzyl)piperidin-4-yl]ethyl]phthalimide

HRID 54548Notes

Reaction equation

HRID 54548 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14]O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:37]1(=[O:47])[NH:41][C:40](=[O:42])[C:39]2=[CH:43][CH:44]=[CH:45][CH:46]=[C:38]12.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][N:41]3[C:40](=[O:42])[C:39]4=[CH:43][CH:44]=[CH:45][CH:46]=[C:38]4[C:37]3=[O:47])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 105618622-(1-(4-Fluorobenzyl)piperidin-4-yl)ethan-1-ol

Product 1

HCID 19959203N-[2-[1-(4-fluorobenzyl)piperidin-4-yl]ethyl]phthalimideYield 59.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1-(4-fluorobenzyl)-4-(2-hydroxyethyl)piperidine (10.0 g), triphenylphosphine (13.04 g) and phthalimide (6.65 g) in tetrahydrofuran (100 ml) was added dropwise a solution of diethyl diazenedicarboxylate (7.7 ml) in tetrahydrofuran (50 ml). After stirring overnight at ambient temperature, the mixture was evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with water and brine, and dried over magnesium sulfate, and evaporated in vacuo. The residue was suspended with hexane--ether (100 ml--100 ml) and the precipitates were removed by filtration. The filtrate was evaporated in vacuo and the residue was recrystallized from hexane to give N-[2-[1-(4-fluorobenzyl)piperidin4-yl]ethyl]phthalimide (9.23 g).

Workup

  1. customthe mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customether (100 ml--100 ml) and the precipitates were removed by filtration
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-f4a788c4f2734079961b23bcc823f8e6
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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