Sodium Chloride → HCID 13064814, compound

HRID 1979766Notes

Reaction equation

HRID 1979766 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.[Cl:14][CH2:15][CH2:16][CH2:17]Br.C(N(CC)CC)C.[Cl-].[Na+]>CN(C)C=O>[Cl:14][CH2:15][CH2:16][CH2:17][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

6

Reactant 4

HCID 5234Sodium ChlorideHCID 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 963874-Phenylpiperidin-4-ol

Product 1

HCID 13064814HCID 13064814, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16.0 Grams of 4-hydroxy-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 layer 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). 14.3 Grams of 1-chloro-3-(4-hydroxy-4-phenyl-1-piperidyl)propane was obtained as in the form of colorless oily substance. Then this oily substance was distilled under a reduced pressure to obtain a fraction of distillate. The fraction of distillate was made as in the form of hydrochloride and recrystallized from ethanol to obtain 1-chloro-3-(4-hydroxy-4-phenyl-1-piperidyl)propane monohydrochloride having the melting point of 192°-195° C. as in the form of colorless needle-like crystals.

Workup

  1. extractionthe organic layer was extracted with chloroform
  2. washthe chloroform layer 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-fd7303bb81af491b8838421ae26166f9
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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