Sodium Chloride → 1-(3-Chloropropyl)-4-phenylpiperidine

HRID 1979765Notes

Reaction equation

HRID 1979765 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][CH2:14][CH2:15][CH2:16]Br.C(N(CC)CC)C.[Cl-].[Na+]>CN(C)C=O>[Cl:13][CH2:14][CH2:15][CH2:16][N:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 698734-Phenylpiperidine

Product 1

HCID 2036891-(3-Chloropropyl)-4-phenylpiperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24 Grams of 4-phenylpiperidine, 24 g of 1-chloro-3-bromopropane and 15 g of triethylamine were mixed with 100 ml of dimethylformamide and stirred at 50°-60° C. for 1 hour. The reaction mixture was poured into 200 ml of saturated sodium chloride aqueous-solution and the organic layer was extracted with chloroform. Then the chloroform layers was washed with water, dried and the chloroform was removed by distillation. The residue thus obtained was purified by a silica-gel column chromatography (to obtain only the main product at the upper-most portion in the column). 15.3 Grams of 1-chloro-3-(4-phenylpiperidinyl)propane was obtained as in the form of colorless oily substance. Then this oily substance was distilled under a reduced pressure to obtain 11 g of a fraction of distillate having the boiling point of 112°-115° C. (0.1 mmHg). A part of this distillate was made as in the form of hydrochloride and recrystallized from ethanol to obtain 1-chloro-3-(4-phenyl-1-piperidyl)propane monohydrochloride having the melting point of 167°-169° C. as in the form of colorless needle-like crystals.

Workup

  1. extractionthe organic layer was extracted with chloroform
  2. washThen the chloroform layers was washed with water
  3. customdried
  4. customthe chloroform was removed by distillation
  5. customThe residue thus obtained
  6. customwas purified by a silica-gel column chromatography (
  7. customto obtain only the main product at the upper-most portion in the column)

Sources & evidence

ORD record
ord-a6e200d02939473886ec8959476baf5e
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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