Hydrochloric Acid → HCID 23458341, compound

HRID 1679985Notes

Reaction equation

HRID 1679985 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][CH:7]([CH:14]1[O:19][CH2:18][C:17](=O)[N:16](C)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:3])=[O:2].[CH3:26]O.Cl>C1COCC1>[N+:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][CH:7]([CH:14]1[O:19][CH2:18][CH2:17][NH:16][CH:15]1[CH3:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 15572629HCID 15572629, compound

Product 1

HCID 23458341HCID 23458341, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a solution of 12.3 g of 2-[α-(2-nitro-phenoxy)-benzyl]-4-methyl-morpholin-5-one in 350 ml of anhydrous THF there was slowly added dropwise 77 ml of a molar solution of BH3 in THF. After the addition, the mixture was refluxed for 6 hours. The excess of BH3 was eliminated with MeOH at room temperature, and dropwise addition was then made to the reaction mixture of 50 ml of 23% HCl and stirring carried out for 1 hour at 60° C. The whole was concentrated to a small volume and the residue diluted with water, thereafter alkalinizing with NaOH and extracting with CH2Cl2. After normal processing and crystallization from isopropyl ether, the 2-[α-(2-nitro-phenoxy)-benzyl]-3-methyl-morpholine, m.p. 78°-81° C. (8.1 g; 68%) was obtained.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for 6 hours
  3. additiondropwise addition
  4. concentrationThe whole was concentrated to a small volume
  5. additionthe residue diluted with water
  6. extractionextracting with CH2Cl2
  7. customAfter normal processing and crystallization from isopropyl ether

Sources & evidence

ORD record
ord-65e100473d0e428b83b010c2cbb1c620
Source dataset
uspto-grants-1981_06
Patent number
US04271160

Reaction notes

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