Dimethylamine → HCID 14458193, compound

HRID 620239Notes

Reaction equation

HRID 620239 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[N:23]([CH2:24][CH2:25][CH2:26]Br)[N:22]=[N:21][N:20]=3)=[CH:14][CH:13]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].[CH3:32][NH:33][CH3:34]>C(#N)C>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]3[N:23]([CH2:24][CH2:25][CH2:26][N:33]([CH3:34])[CH3:32])[N:22]=[N:21][N:20]=3)=[CH:14][CH:13]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 14458189HCID 14458189, compound

Product 1

HCID 14458193HCID 14458193, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

5-[(4-((4-Acetyl-3-hydroxy-2-propylphenyl)methoxy)phenyl)methyl]-1-(3-bromopropyl)-1H-tetrazole (2.0 g, 0.004 mol) was added to acetonitrile (40 ml). Dimethylamine (large excess) was cooled in the unopened reagent bottle then added to the acetonitrile solution. The mixture was cooled and stirred at 0° C. for 5 hours then concentrated in vacuo. Water was added to the concentrate and the aqueous solution was extracted with ethyl acetate. The ethyl acetate layers were combined, washed with water, dried over sodium sulfate, filtered, and concentrated to dryness in vacuo. The residue was chromatographed by HPLC (preparatory-scale, silica gel column, eluted isocratically with a mixture of 9.5:0.5% methylene chloride:methanol plus 0.5% diethylamine added) to yield 1.4 g, 77.8% yield of the title product as a yellow oil; n.m.r. (300 MHz, CDCl3) δ: 1.0 (t, 3H); 1.6 (m, 2H); 1.9 (m, 2H); 2.1 (s, 6H; m, 2H); 2.6 (s, 3H); 2.65 (t, 2H); 4.2 (t, 2H); 4.3 (s, 2H); 5.1 (s, 2H); 6.9 (d, 2H); 7.0 (d, 1H); 7.15 (d, 2H); 7.6 (d, 1H); 12.7 (s, 1H).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationthen concentrated in vacuo
  3. additionWater was added to the
  4. concentrationconcentrate
  5. extractionthe aqueous solution was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness in vacuo
  10. customThe residue was chromatographed by HPLC (preparatory-scale, silica gel column
  11. washeluted isocratically with a mixture of 9.5
  12. addition0.5% methylene chloride:methanol plus 0.5% diethylamine added)

Sources & evidence

ORD record
ord-d218a5599cf6431e9d0d7d4b2b82622c
Source dataset
uspto-grants-1989_04
Patent number
US04820722

Reaction notes

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