Triphenylphosphine → C-[5-Chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-yl]-methylamine

HRID 1959575Notes

Reaction equation

HRID 1959575 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([Cl:19])[C:10]=1[CH2:11][O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[Cl:19][C:9]1[C:10]([CH2:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)=[C:5]([CH2:4][NH2:1])[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 441904763-Azidomethyl-5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridine

Product 1

HCID 67077948C-[5-Chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-yl]-methylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-azidomethyl-5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridine (0.46 g, 1.6 mmol) and triphenylphosphine (0.43 g, 1.6 mmol) in THF (15 mL) and H2O (0.15 mL) was stirred at RT overnight. Solvents were concentrated in vacuo and the residue was partitioned between DCM (10 mL) and saturated NaHCO3 solution (10 mL). After extraction of the aqueous layer with DCM (2×10 mL) the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The resulting title compound was used for the next reaction without purification. MS (m/z): 256.8 [M+H+].

Workup

  1. concentrationSolvents were concentrated in vacuo
  2. customthe residue was partitioned between DCM (10 mL) and saturated NaHCO3 solution (10 mL)
  3. extractionAfter extraction of the aqueous layer with DCM (2×10 mL) the combined organic layers
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting title compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-5b93abd7fa964f58b5c13267956e6279
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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