Triphenylphosphine → HCID 20306038, compound

HRID 1732344Notes

Reaction equation

HRID 1732344 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:11][CH2:12][OH:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].O[C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18]([NH2:20])=[O:19].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([O:10][CH2:11][CH2:12][O:13][C:23]2[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3424033-HydroxybenzamideHCID 14022405HCID 14022405, compound

Product 1

HCID 20306038HCID 20306038, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Acetyl-4-(2-hydroxyethoxy)piperidine (5.0 g.), 3-hydroxybenzamide (4.4 g.), diethyl azodicarboxylate (5.6 g.) and triphenylphosphine (8.4 g.) in dry tetrahydrofuran (100 ml.) were stirred at 0° C. for 2 hours then at room temperature for 64 hours. The solvent was evaporated in vacuo, then the residue treated with refluxing ether (3×100 ml.) and the mother liquors decanted. The residual oil was taken up in chloroform and washed with dilute sodium hydroxide solution (40 ml.) and water (40 ml.). The chloroform layer was dried (MgSO4) then the solvent evaporated in vacuo. The residual oil was treated with ether (50 ml.) and set aside in the fridge. The resulting solid was collected, slurried with ether (30 ml.), filtered and the solid washed with ether (30 ml.) to give 4-[2-(N-acetyl-4-piperidyloxy)ethoxy]benzamide (3.7 g.) containing some triphenylphosphine oxide (approximately 25% by n.m.r.).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe residue treated with refluxing ether (3×100 ml.)
  3. customthe mother liquors decanted
  4. washwashed with dilute sodium hydroxide solution (40 ml.) and water (40 ml.)
  5. dry with materialThe chloroform layer was dried (MgSO4)
  6. customthe solvent evaporated in vacuo
  7. additionThe residual oil was treated with ether (50 ml.)
  8. customThe resulting solid was collected
  9. filtrationfiltered
  10. washthe solid washed with ether (30 ml.)

Sources & evidence

ORD record
ord-16ec7e3e762b4d939589fa7de4988084
Source dataset
uspto-grants-1980_12
Patent number
US04237138

Reaction notes

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