Dicyclohexylamine → Dichloro(dicyclohexylamino)phosphine

HRID 1884169Notes

Reaction equation

HRID 1884169 reaction equation
[P:1]([Cl:4])(Cl)[Cl:2].[NH:5]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.N(C1CCCCC1)C1CCCCC1.Cl>CCCCCC>[N:5]([P:1]([Cl:4])[Cl:2])([CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 24387Phosphorus trichlorideHCID 2793652Dicyclohexylamine hydrochloride

Product 1

HCID 13311825Dichloro(dicyclohexylamino)phosphineYield 77%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 34.4 g (0.25 moles) of PCl3 in 400 mL of hexane was treated with Cy2NH (90.7 g, 0.50 moles) dropwise at ° C. for 30 min. The resulting white slurry was warmed to room temperature and stirred for 1 h, refluxed overnight before removal of Cy2NH—HCl by filtration. The white solids were washed with hexane (2×100 mL). The combined filtrates were concentrated to give the crude Cy2N—PCl2 (54.0 g, 77% yield). 31P NMR (121 MHz, CD2Cl2): δ171.3 (s) ppm.

Workup

  1. washThe white solids were washed with hexane (2×100 mL)
  2. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-6c60c341c08048fa87766dce1af6d968
Source dataset
uspto-grants-2004_07
Patent number
US06762330B2

Reaction notes

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