Triethylamine → 3-(4-Propyl-heptyl)-4-(5-hydroxypentyl)morpholine

HRID 329903Notes

Reaction equation

HRID 329903 reaction equation
[CH2:1]([CH:4]([CH2:14][CH2:15][CH3:16])[CH2:5][CH2:6][CH2:7][CH:8]1[CH2:13][O:12][CH2:11][CH2:10][NH:9]1)[CH2:2][CH3:3].C(N(CC)CC)C.[Cl-].C[O:26][C:27](=O)[CH2:28][CH2:29][CH2:30][C:31](O)=O.Cl.C(N(CC)CC)C>CCOCC.C1C=CC=CC=1>[CH2:14]([CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH:8]1[CH2:13][O:12][CH2:11][CH2:10][N:9]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][OH:26])[CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 110963433-(4-Propylheptyl)morpholineHCID 53445129Glutaric acid monomethylester chloride

Product 1

HCID 147219973-(4-Propyl-heptyl)-4-(5-hydroxypentyl)morpholine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 8.0 grams (0.035 moles) of 3-(4-propyl-heptyl)-morpholine, 4 grams of triethylamine, 5.8 grams (0.035 moles) of glutaric acid-monomethylesterchloride and 100 ml. of benzene were refluxed for 3 hours. After cooling the triethylamine hydrochloride formed was removed by filtration and the benzene solution was directly admixed with 12 grams of lithium aluminum hydride in 500 ml of ether. The reaction mixture was refluxed for 8 hours and decomposed by slow addition of water and sodium hydroxide. The precipitate was filtered off. The ether solution was dried and evaporated to dryness and the residue was distilled at 144°-146° C./ 0.01 mm Hg.; yield 9.8 grams (89%). The base obtained was dissolved in ether and the hydrochloride precipitated with hydrochloric acid in ethanol. After recrystallization from ethylacetate/ether, the melting point was 59°-60° C.

Workup

  1. customformed
  2. customwas removed by filtration
  3. temperatureThe reaction mixture was refluxed for 8 hours
  4. additiondecomposed by slow addition of water and sodium hydroxide
  5. filtrationThe precipitate was filtered off
  6. dry with materialThe ether solution was dried
  7. customevaporated to dryness
  8. distillationthe residue was distilled at 144°-146° C./ 0.01 mm Hg
  9. customThe base obtained
  10. customthe hydrochloride precipitated with hydrochloric acid in ethanol
  11. customAfter recrystallization from ethylacetate/ether

Sources & evidence

ORD record
ord-4c14020038ae41a6a62069f37120219d
Source dataset
uspto-grants-1990_01
Patent number
US04894221

Reaction notes

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