Benzyl Alcohol → HCID 20289417, compound

HRID 1413999Notes

Reaction equation

HRID 1413999 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][N:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:5][CH:6]1[O:8][CH2:7]1.[CH2:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O1CCOCC1.[H-].[Na+]>O>[C:18]1([CH2:17][O:24][CH2:7][CH:6]2[CH2:5][N:4]([CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:3][CH:2]([CH2:16][OH:1])[O:8]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 312751,4-DioxaneHCID 14385393HCID 14385393, compound

Product 1

HCID 20289417HCID 20289417, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.48 G (0.025 mole) of N,N-bis(2,3-epoxypropyl)benzylamine is added to a mixture of 2.70 g (0.025 mole) of benzyl alcohol in 75 ml of dioxane containing 1 equivalent of sodium hydride. The reaction is allowed to cool below 40° with an ice-bath for approximately 1/2 hour and is then heated at reflux overnight. After cooling to room temperature, the entire mixture is poured slowly, with stirring, into 150 ml of water. The aqueous mixture is extracted with 3×125 ml portions of chloroform. The CHCl3 extracts are combined, washed with 200 ml of water and 200 ml of saturated NaCl solution. The CHCl3 layer is then dried over anhydrous NaSO4, evaporated in vacuo to yield 6.1 g (74%) of crude product as a pale yellow oil. The oil is chromatographed on 300 g of neutral Alumina III to give 5.6 g (68%) of 6-[(phenylmethoxy)methyl]-4-(phenylmethyl)-2-morpholinemethanol.

Workup

  1. temperatureto cool below 40° with an ice-bath for approximately 1/2 hour
  2. temperatureis then heated
  3. temperatureat reflux overnight
  4. additionthe entire mixture is poured slowly
  5. extractionThe aqueous mixture is extracted with 3×125 ml portions of chloroform
  6. washwashed with 200 ml of water and 200 ml of saturated NaCl solution
  7. dry with materialThe CHCl3 layer is then dried over anhydrous NaSO4
  8. customevaporated in vacuo
  9. customto yield 6.1 g (74%) of crude product as a pale yellow oil
  10. customThe oil is chromatographed on 300 g of neutral Alumina III

Sources & evidence

ORD record
ord-6be4d5505d4448b48e2294420870add3
Source dataset
uspto-grants-1981_02
Patent number
US04252801

Reaction notes

Loading…