4-Methylmorpholine → HCID 10564036, compound

HRID 1377903Notes

Reaction equation

HRID 1377903 reaction equation
[C:1]1([C:7]2[CH:19]=[CH:18][C:10]([O:11][CH2:12][CH2:13][CH2:14][C:15](O)=[O:16])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CCOCC1.Cl.[NH2:28][OH:29].C1COCC1>S(Cl)(Cl)=O.O>[C:1]1([C:7]2[CH:19]=[CH:18][C:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]([NH:28][OH:29])=[O:16])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 443297Hydroxyamine hydrochlorideHCID 15675487HCID 15675487, compound

Product 1

HCID 10564036HCID 10564036, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 4-(4-phenylphenoxy)butanoic acid (2.42 g, 9.45 mmol) in thionyl chloride (25 mL) was heated at reflux for 90 minutes, during which time the mixture became homogenous. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was taken up in 1:1 methylene chloride/THF. In a separate flask 4-methylmorpholine (3.5 mL, 32 mmol) was added to a solution of hydroxylamine hydrochloride (2.1 g, 30 mmol) in water (10 mL). THF (20 mL) was then added and the hydroxylamine solution was decanted into the acid chloride solution, and the reaction mixture was vigorously stirred for 2 hours. The reaction mixture was partitioned between saturated aqueous NH4Cl and methylene chloride. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 4-(4-phenylphenoxy)butanohydroxamic acid (1.45 g) as a white solid. 1H NMR (DMSO-d6) δ 1.94 (m, 2H), 2.14 (t, 2H, J=7 Hz), 4.01 (t, 2H, J=6 Hz), 7.02 (d, 2H, J=8 Hz), 7.29 (t, 1H, J=6 Hz), 7.43 (t, 2H, J=6 Hz), 7.62 (m, 4H), 8.71 (s, 1H), 10.44 (s, 1H). MS (DCI/NH3) 289 (M+NH4+, 100), 272 (M+H+, 35), 255 (30). Anal. Calcd for: C16H17NO3 : C, 70.83; H, 6.32; N, 5.16. Found: C, 64.81; H, 6.65; N, 5.82.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 90 minutes, during which time the mixture
  3. concentrationconcentrated in vacuo
  4. customthe hydroxylamine solution was decanted into the acid chloride solution
  5. customThe reaction mixture was partitioned between saturated aqueous NH4Cl and methylene chloride
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a2b983daea240b9bb4cefc2a27501e1
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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