Potassium Carbonate → HCID 13773057, compound

HRID 235792Notes

Reaction equation

HRID 235792 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[OH:14].[CH2:15]([CH:17]1[O:19][CH2:18]1)Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[O:14][CH2:15][CH:17]1[O:19][CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 137730562-Chloro-3-(piperidin-1-yl)phenol

Product 1

HCID 13773057HCID 13773057, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7.47 grams of 2-chloro-3-piperidinophenol, 29.00 grams of epibromohydrin, 28.79 grams of potassium carbonate and 400 ml of acetonitrile is heated to reflux for twenty hours, insoluble matters are removed therefrom by filtration, the filtrate is entirely concentrated to dryness, and the residue is purified by a silica gel chromatography followed by recrystallization from n-hexane to give 8.0 grams (85%) of 1-(2-chloro-3-piperidinophenoxy)-2,3-epoxypropane as colorless crystals of m.p. 55°-57° C. NMR (CDCl3): δ 1.55-1.95 (m, 6H), 2.75-3.19 (m, 7H), 4.10 (dd, 1H, J=11 Hz and 14 Hz), 4.18 (dd, 1H, J=11 Hz and 21 Hz), 6.54-6.77 (m, 2H). Elementary analysis calculated as C14H18ClNO2 : C 62.80, H 6.78, N 5.23, Cl 13.24; Found: C 62.61, H 6.87, N 5.08, Cl 13.15.

Workup

  1. temperatureis heated
  2. temperatureto reflux for twenty hours
  3. custominsoluble matters are removed
  4. filtrationby filtration
  5. concentrationthe filtrate is entirely concentrated to dryness
  6. customthe residue is purified by a silica gel chromatography
  7. customfollowed by recrystallization from n-hexane

Sources & evidence

ORD record
ord-7f74458c088f4423853e01f48d62ab18
Source dataset
uspto-grants-1987_02
Patent number
US04642307

Reaction notes

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