Hydrochloric Acid → HCID 15572617, compound

HRID 903959Notes

Reaction equation

HRID 903959 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[O:6][CH:7]([CH:14]1[O:19][CH2:18][CH2:17][NH:16][C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:3])=[O:2].CO.Cl>C1COCC1>[N+:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[O:6][CH:7]([CH:14]1[O:19][CH2:18][CH2:17][NH:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 15572616HCID 15572616, compound

Product 1

HCID 15572617HCID 15572617, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 33 g of 2-[α-(2-nitro-phenoxy)-benzyl]-morpholin-3-one dissolved in 60 ml of anhydrous THF there was added dropwise under stirring 16.7 ml of a 0.9 M solution of BH3 in THF. The whole was heated at reflux for 3 hours and dropwise addition under cold conditions (0°-5° C.) was then made of 3 ml of methanol and then of 3 ml of 23% HCl. The solvent was removed under reduced pressure. The residue was diluted with H2O, made alkaline and extracted with chloroform. The organic extracts were washed to neutrality, dried and evaporated to dryness, to obtain 28.6 g of 2-[α-(2-nitrophenoxy)-benzyl]-morpholine. Yield 94%.

Workup

  1. additionwas added dropwise
  2. temperatureThe whole was heated
  3. temperatureat reflux for 3 hours
  4. additiondropwise addition under cold conditions (0°-5° C.)
  5. customThe solvent was removed under reduced pressure
  6. additionThe residue was diluted with H2O
  7. extractionextracted with chloroform
  8. washThe organic extracts were washed to neutrality
  9. customdried
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-5f8ba4ef836d40e495a2845d11fcbc99
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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