Morpholine → HCID 23469680, compound

HRID 128354Notes

Reaction equation

HRID 128354 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6](O)[CH:7]([CH3:9])[CH3:8])=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>O>[CH3:8][CH:7]([CH3:9])[CH:6]([C:5]1[CH:11]=[CH:12][C:2]([OH:1])=[CH:3][CH:4]=1)[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 14512393HCID 14512393, compound

Product 1

HCID 23469680HCID 23469680, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4-hydroxy-α-isopropylbenzyl alcohol (1.0 g; 0.006 mol) morpholine (1.3 g; 0.015 mol) and water (1.3 ml) is refluxed under a nitrogen atmosphere for 23 hours, and then poured into water (~20 ml). The aqueous solution is extracted with 30 ml of ether, the ethereal solution dried over magnesium sulfate, and concentrated to give 0.97 g of crude product (69% of theory). Recrystallization of the crude product from methylene chloride affords pure title compound (490 mg 35%): mp 142°-143° C.; IR (Nujol) 3300 (s), 2940 (s), 1610 (m), 1595 (m) cm-1 ; NMR (CDCl3) δ0.75 and 0.92 (a pair of d, J=7 Hz, 6 H, two methyls), 1.8-2.4 (m, 1 H, isopropyl methine proton), 2.3-2.5 (m, 4 H, two methylene groups adjacent to the nitrogen atom), 2.94 (d, J=8 Hz, 1 H, benzylic proton), 3.6-3.9 (m, 4 H, two methylene groups adjacent to the oxygen atom), 3.9-6.2 (broad s, 1 H, phenoxy proton) and 6.75 and 7.05 ppm (AB quartet, J=8 Hz, 4 H, aromatic). Anal. Calcd for C14H21NO2 : C, 71.45; H, 8.95; N, 5.95. Found: C, 71.07; H, 8.64; N, 6.01.

Workup

  1. temperatureis refluxed under a nitrogen atmosphere for 23 hours
  2. extractionThe aqueous solution is extracted with 30 ml of ether
  3. dry with materialthe ethereal solution dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give 0.97 g of crude product (69% of theory)
  6. customRecrystallization of the crude product from methylene chloride

Sources & evidence

ORD record
ord-6e68210c5c8347228064b69d649788b6
Source dataset
uspto-grants-1981_03
Patent number
US04259486

Reaction notes

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