Triphenylphosphine → 3-(Pyridin-4-yl)propan-1-amine

HRID 1458954Notes

Reaction equation

HRID 1458954 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][N:10]=[N+]=[N-])=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C1COCC1.CCOC(C)=O>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][NH2:10])=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 22097685HCID 22097685, compound

Product 1

HCID 143474663-(Pyridin-4-yl)propan-1-amine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-4 (7.3 g, 41.2 mmol) in H2O (100 mL) and THF (200 mL) was treated with triphenylphosphine (43.3 g, 165 mmol) and the resulting slurry was stirred vigorously for 24 h. The solution was diluted with EtOAc and washed with 10% KHSO4. The aqueous layers were combined and basified to pH13 with 1N NaOH and extracted repeatedly with CH2 Cl2. The CH2Cl2 layers were combined, dried with brine and concentrated to give 2-5 as a yellow oil.

Workup

  1. washwashed with 10% KHSO4
  2. extractionextracted repeatedly with CH2 Cl2
  3. dry with materialdried with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-03d8e686b14c4846af6cf63f71261c3b
Source dataset
uspto-grants-1998_12
Patent number
US05852045

Reaction notes

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