1-Bromo-3-chloropropane → HCID 13064814, compound

HRID 2420529Notes

Reaction equation

HRID 2420529 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH2:15][CH2:16][CH2:17][Cl:18]>[OH-].[Na+].CC(C)=O>[Cl:18][CH2:17][CH2:16][CH2:15][N:5]1[CH2:6][CH2:7][C:2]([OH:1])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 963874-Phenylpiperidin-4-ol

Product 1

HCID 13064814HCID 13064814, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-hydroxy-4-phenylpiperidine (35.4 g, 0.2 mole) in 50 ml of 20% NaOH and 250 ml of acetone was cooled at <15° and 1-bromo-3-chloropropane (31.4 g, 0.2 mole) was added dropwise. The mixture was stirred at room temperature for 18 hours and concentrated in vacuo at <40°. The concentrate was converted to the HCl salt with HCL(g)/2-PrOH and concentrated in vacuo to an oil. The oil crystallized in hot acetone and the solid salt was collected and dried. The salt was warmed in 2-PrOH, cooled and filtered to remove 8 g of quaternary salt. mp >260°. The filtrate was warmed and diluted with ethyl acetate to obtain the desired salt. Yield 13 g (22.5%), m.p. 173°-6° (dec.).

Workup

  1. concentrationconcentrated in vacuo at <40°
  2. concentrationconcentrated in vacuo to an oil
  3. customThe oil crystallized in hot acetone
  4. customthe solid salt was collected
  5. customdried
  6. temperatureThe salt was warmed in 2-PrOH
  7. temperaturecooled
  8. filtrationfiltered
  9. customto remove 8 g of quaternary salt
  10. temperatureThe filtrate was warmed
  11. additiondiluted with ethyl acetate

Sources & evidence

ORD record
ord-d156e2f6317846b4b59252ac5998947d
Source dataset
uspto-grants-1978_08
Patent number
US04110536

Reaction notes

Loading…