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Hydrochloric Acid → HCID 13851158, compound

HRID 2231730
Notes
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Reaction equation

HRID 2231730 reaction equation
[ClH:1].[C:2]1([CH:8]2[O:13][CH2:12][CH2:11][NH:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](=O)[CH3:28])=[CH:22][CH:21]=1)([O:16][CH3:17])=[O:15].C([BH3-])#N.[Na+].Cl>CO.ClCCl.C(OCC)C>[ClH:1].[CH3:17][O:16][C:14](=[O:15])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH:27]([N:10]2[CH2:11][CH2:12][O:13][CH:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9]2)[CH3:28])=[CH:22][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 123435392-Phenylmorpholine hydrochlorideHCID 13851156Methyl 2-(4-(2-oxopropyl)phenoxy)acetate

Product 1

HCID 13851158HCID 13851158, compound

Reagents, catalysts & solvents 3

HCID 887
Methanol
Solvent
2×
HCID 3283Diethyl EtherSolvent
HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-phenylmorpholine hydrochloride (6.05 g), 1-(4-carbomethoxymethoxyphenyl)propan-2-one (6.63 g) and sodium cyanoborohydride (1.61 g) in methanol (100 ml) was stirred at room temperature for 22 hours. The solvent was removed under reduced pressure and aqueous sodium bicarbonate solution added to the residue and extracted with dichloromethane (X2). The extracts were washed with aqueous sodium bicarbonate, dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated to dryness to give an oil. Chromatography on silica gel in 0→7% methanol in dichloromethane gave an oil which was dissolved in diethyl ether and treated with an ethereal solution of hydrogen chloride. Evaporation to dryness and trituration of the residue with ethyl acetate gave a solid. Recrystallisation of this solid gave the title compound, m.p. 187°-190° C. (methanol-ethyl acetate), of analytical purity.

Workup

  1. customThe solvent was removed under reduced pressure and aqueous sodium bicarbonate solution
  2. additionadded to the residue
  3. extractionextracted with dichloromethane (X2)
  4. washThe extracts were washed with aqueous sodium bicarbonate
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customthe filtrate evaporated to dryness
  8. customto give an oil
  9. customEvaporation to dryness and trituration of the residue with ethyl acetate
  10. customgave a solid
  11. customRecrystallisation of this solid

Sources & evidence

ORD record
ord-34f67e99cc894145a537713ed6c14ab7
Source dataset
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04783460

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes