2-Propylpyridine → HCID 10884415, compound

HRID 1422065Notes

Reaction equation

HRID 1422065 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](=[O:16])[CH2:14][Br:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH2:20][CH3:21]>CC(C)=O>[Br-:15].[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](=[O:16])[CH2:14][N+:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH2:19][CH2:20][CH3:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 693202-PropylpyridineHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 10884415HCID 10884415, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-benzyloxyphenacylbromide (15.7 g, 51 mmol) and 2-n-propylpyridine (12 ml, 108 mmol) in 75 ml of dry acetone was heated to reflux for four days. The mixture was cooled and the precipitate was isolated and dried to afford 17.34 g of 1-(4-benzyloxyphenacyl)-2-n-propylpyridinium bromide. The quaternary salt (17.34 g) was suspended in 250 ml of water and sodium hydrogen carbonate (17.1 g) was added. The mixture was refluxed for three hours. The resulting precipitate was filtered off, washed with water and dried to an overall yield of 12.86 g (77%) of 2-(4-benzyloxyphenyl)-1-ethylindolizine. M.p. 106-108° C. MS(SP): m/z 328 (M+1). 1H-NMR (DMSO-d6, 200 MHz) δ: 1.10 (t, 3H); 2.81 (q, 2H); 5.13 (s, 2H); 6.48 (dd, 1H); 6.61 (dd, 1H); 7.08 (d, 2H); 7.31-7.45 (m, 6H); 7.49 (d, 2H); 7.56 (s, 1H); 8.13 (d, 1H). Analysis: Calculated for C23H21N1O1 : C, 84.37; H, 6.48; N, 4.28%; Found: C, 84.33; H, 6.51; N, 4.17%.

Workup

  1. temperatureto reflux for four days
  2. temperatureThe mixture was cooled
  3. customthe precipitate was isolated
  4. customdried

Sources & evidence

ORD record
ord-71f48baada614b8b9a95f61a2d947752
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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