Phosphorus tribromide → HCID 67946345, compound

HRID 359116Notes

Reaction equation

HRID 359116 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][Br:16])[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)Br.C1(C2CCN(CCCO)CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)Cl>[BrH:16].[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][Br:16])[CH2:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 24614Phosphorus tribromideHCID 12725720HCID 12725720, compoundHCID 14476400HCID 14476400, compound

Product 1

HCID 67946345HCID 67946345, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

3-(4-Phenyl-1,2,3,6-tetrahydro-1-pyridyl)-1-bromopropane may be prepared in the following manner: 2.7 cc of phosphorus tribromide is added to a vigorously agitated solution of 3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)-1-propanol (8.7 g) in toluene (100 cc) in the course of 5 minutes and at a temperature close to 20° C. The suspension is heated to a temperature close to 111° C. for 2 hours. After cooling to a temperature close to 20° C., the suspension is filtered, the precipitate obtained is dissolved in methylene chloride (250 cc). The organic phase is washed with distilled water (150 cc), dried over anhydrous magnesium sulphate then concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa). 14 g of 3-(4-phenyl--1,2,3,6-tetrahydro-1-pyridyl)1-bromopropane hydrobromide are obtained, melting at 185° C.

Workup

  1. customclose to 20° C
  2. temperatureThe suspension is heated to a temperature
  3. customclose to 111° C. for 2 hours
  4. temperatureAfter cooling to a temperature
  5. customclose to 20° C.
  6. filtrationthe suspension is filtered
  7. customthe precipitate obtained
  8. washThe organic phase is washed with distilled water (150 cc)
  9. dry with materialdried over anhydrous magnesium sulphate
  10. concentrationthen concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa)

Sources & evidence

ORD record
ord-02c15babf11b42279d13efbef9b688f7
Source dataset
uspto-grants-1991_03
Patent number
US04999355

Reaction notes

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