Triphenylphosphine → HCID 19022621, compound

HRID 1034453Notes

Reaction equation

HRID 1034453 reaction equation
[N:1]([CH:4]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]=2[NH:6][C:5]1=[O:23])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:1][CH:4]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]=2[NH:6][C:5]1=[O:23]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 19022644HCID 19022644, compound

Product 1

HCID 19022621HCID 19022621, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,3,4,5-tetrahydro-3-azido-4-(4-methoxyphenyl)-1H-1-benzazepin-2-one (170 mg, 0.552 mmol) in 5 mL of wet tetrahydrofuran was treated with triphenylphosphine (256 mg, 1 mmol, 1.8eq) and the resulting mixture heated at reflux for 6 hours, then cooled to room temperature. The solvent was removed under vacuum and the residue was purified on a silica gel column (eluant 10% MeOH/CH2Cl2) to give the product in quantitative yield. 1H NMR (400 MHz, CDCl3): 1.35 (br s, 2H), 2.90 (dd; 6,13 Hz; 1H), 3.05 (dd; 12, 13 Hz; 1H), 3.67 (m, 2H), 3.77 (s, 3H), 6.84 (d, 8Hz, 2H), 7.01 (d, 8 Hz, 1H), 7.13-7.30 (m, 5H), 8.22 (br s, 1H). FAB-MS: calculated for C17H18N2O2 282; found 283 (40%).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 6 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified on a silica gel column (eluant 10% MeOH/CH2Cl2)
  5. customto give the product in quantitative yield

Sources & evidence

ORD record
ord-9dda5f2230ff4dfb9dec375c6aab3d72
Source dataset
uspto-grants-1994_05
Patent number
US05317017

Reaction notes

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