Water → 5-Bromopentanoic acid, morpholide

HRID 2203523Notes

Reaction equation

HRID 2203523 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(N(CC)CC)C.O>C1COCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8471TriethylamineHCID 5211735-Bromovaleryl chloride

Product 1

HCID 5318495-Bromopentanoic acid, morpholideYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 5-bromovaleryl chloride (4.0 mL, 30 mmol) was added dropwise to a solution of morpholine (3.13 mL, 36 mmol) and triethylamine (6.25 mL, 45 mmol) in anhydrous THF (200 mL), and the reaction was stirred for 3.5 hours. Water (100 mL) was added, and the resulting solution was extracted with ethyl acetate (250 mL+150 mL). The combined extracts were washed with aqueous hydrogen chloride (100 mL of 1 N), water (60 mL), and brine (100 mL); dried over magnesium sulfate; filtered; concentrated under reduced pressure; and further dried under high vacuum to provide 6.60 g of 4-(5-bromopentanoyl)morpholine as a yellow oil.

Workup

  1. extractionthe resulting solution was extracted with ethyl acetate (250 mL+150 mL)
  2. washThe combined extracts were washed with aqueous hydrogen chloride (100 mL of 1 N), water (60 mL), and brine (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customand further dried under high vacuum

Sources & evidence

ORD record
ord-879d6491e4d148a585e36b787ed00e03
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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