Sulfuric Acid → HCID 14721994, compound

HRID 329902Notes

Reaction equation

HRID 329902 reaction equation
C(C(CCC)CCCC(NCC1C=CC=CC=1)CO)CC.C1OC1.O[CH2:26][CH2:27][N:28]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH:29]([CH2:32][CH2:33][CH2:34][CH:35]([CH2:39][CH2:40][CH3:41])[CH2:36][CH2:37][CH3:38])[CH2:30][OH:31].S(=O)(=O)(O)O.[OH-].[Na+]>C(O)C>[CH2:42]([N:28]1[CH2:27][CH2:26][O:31][CH2:30][CH:29]1[CH2:32][CH2:33][CH2:34][CH:35]([CH2:39][CH2:40][CH3:41])[CH2:36][CH2:37][CH3:38])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6354Ethylene OxideHCID 14798Sodium HydroxideHCID 14721993HCID 14721993, compoundHCID 198702752-[Benzyl(2-hydroxyethyl)amino]-6-propylnonan-1-ol

Product 1

HCID 14721994HCID 14721994, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

46.6 grams (0.16 mole) of 6-propyl-2-benzylamino-1-nonanol and 11 grams (0.20 moles) of ethylene oxide in 200 ml. 96% ethanol were kept at 100° C. in an autoclave with careful stirring for three hours. The reaction mixture was evaporated. 57 grams (100%) of GLC-unitary substance were obtained, viz. N-(2-hydroxyethyl)-6-propyl-2-benzylamino-1nonanol. Said 57 grams were dissolved in 450 ml. of 70% (w/w) sulfuric acid and kept in a glass autoclave at 140°-150° C. for 15 hours. The reaction mixture was admixed with an excess of 40% aqueous NaOH and extracted with diethyl ether. The ether extract was dried over sodium sulphate and evaporated. Distillation gave 49.7 grams (93 %) N-benzyl-3-(4-propylheptyl)morpholine, boiling point 163°-165° C./0.01mm Hg. This substance (49.7 grams) and 3 grams of 10% (w/w) Pd-C in 500 ml. 96 % ethanol were hydrogenated in a steel autoclave at 100° C. and 100 atmospheres hydrogen pressure for 12 hours. Conventional processing gave 34.2 grams (96%) of 3-(4-propylheptyl)morpholine, boiling point 76°-78° C./0.01 mm Hg. The base obtained was dissolved in ether and the hydrochloride precipitated with hydrochloric acid in ethanol. Recrystallization gave crystals having a melting point of 118°-119° C.

Workup

  1. customwere kept at 100° C. in an autoclave
  2. customThe reaction mixture was evaporated
  3. custom57 grams (100%) of GLC-unitary substance were obtained
  4. dissolutionwere dissolved in 450 ml
  5. extractionextracted with diethyl ether
  6. extractionThe ether extract
  7. dry with materialwas dried over sodium sulphate
  8. customevaporated
  9. distillationDistillation

Sources & evidence

ORD record
ord-bc152e439a6e4a85b34897ce3ffbacf7
Source dataset
uspto-grants-1990_01
Patent number
US04894221

Reaction notes

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