Triphenylphosphine → [trans-4-(2,4-Dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl amine

HRID 1172331Notes

Reaction equation

HRID 1172331 reaction equation
[N:1]([CH2:4][C:5]1[CH2:10][C@@H:9]([N+:11]([O-:13])=[O:12])[C@H:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[CH2:7][CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[C@H:8]1[C@H:9]([N+:11]([O-:13])=[O:12])[CH2:10][C:5]([CH2:4][NH2:1])=[CH:6][CH2:7]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 1317284231-[trans-4-(Azidomethyl)-6-nitrocyclohex-3-en-1-yl]-2,4-dichlorobenzene

Product 1

HCID 68769505[trans-4-(2,4-Dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl amine

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
65 °C

Procedure

To a solution of Example 12B (700 mg, 2.14 mmol) in mixture of tetrahydrofuran/H2O (15 mL/1.5 mL), triphenylphosphine (1.12 mg, 4.28 mmol) was added at room temperature. The reaction mixture was heated to 65° C. for five hours. It was cooled to room temperature, concentrated under reduced pressure, azeotroped with toluene, and purified by flash chromatography (eluting with 10% methanol/CH2Cl2) to provide the title compound. 1H NMR (500 MHz, methanol-d4) δ ppm 7.41-7.48 (m, 2H), 7.28-7.35 (m, 1H), 5.72 (m, 1H), 5.26-5.38 (m, 1H), 3.93-4.04 (m, 1H), 3.17-3.42 (m, 4H), 2.72-2.84 (m, 2H). MS (DCI) m/z 301 (M+H)+.

Workup

  1. additionwas added at room temperature
  2. temperatureIt was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customazeotroped with toluene
  5. custompurified by flash chromatography (eluting with 10% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-8010022cb7ec4e0694010b02430f0a63
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

Loading…