Hydrochloric Acid → Di(4-fluorophenyl) Piperidine-2-phosphonate Hydrochloride

HRID 1077569Notes

Reaction equation

HRID 1077569 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][P:15]([O-:24])[O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:10][CH:9]=1.[ClH:25]>C(Cl)Cl.CCOCC>[ClH:25].[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[P:15]([O:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)(=[O:24])[O:14][C:11]1[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 19431395Di(4-fluorophenyl)phosphite

Product 1

HCID 86749713Di(4-fluorophenyl) Piperidine-2-phosphonate HydrochlorideYield 54%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of piperidine trimer (4.5 g, 54 mmole) and di(4-fluorophenyl)phosphite (14.8 g, 55 mmole) was heated at 90°-100° C. for 3 h under nitrogen. The resulted oil was cooled and dissolved in a mixture of 50 mL CH2Cl2 and 50 mL ether. The solution was saturated with dry HCl, the oil was separated and solidified after several hours. The solid was filtered, washed with ether and dried. The hygroscopic material was stirred in 200 mL dry ether for several hours and the yellowish solid was filtered and dried. The product was obtained in 54% yield (11.6 g) and used for subsequent reaction: mp. 155°-165° C. (dec); 1H NMR (D2O) δ7.2-6.8 (m, 8H), 3.6-2.9 (m, 3H), 2.2-1.4 (m, 6H); MS (FAB) m/e 354 (M-Cl)+. Anal. (exact mass, HRMS) calcd. for C17H19N1O3P1Cl2 m/e 354.1070, found 354.1098.

Workup

  1. temperaturewas heated at 90°-100° C. for 3 h under nitrogen
  2. temperatureThe resulted oil was cooled
  3. customthe oil was separated
  4. waitsolidified after several hours
  5. filtrationThe solid was filtered
  6. washwashed with ether
  7. customdried
  8. filtrationthe yellowish solid was filtered
  9. customdried
  10. customThe product was obtained in 54% yield (11.6 g)
  11. customused for subsequent reaction

Sources & evidence

ORD record
ord-f4d6416951d34911a48cf4f05f706e1d
Source dataset
uspto-grants-1996_08
Patent number
US05543396

Reaction notes

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