1-Bromo-3-chloropropane → 4-(3-Chloropropyl)morpholine

HRID 1453783Notes

Reaction equation

HRID 1453783 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4]Br.[NH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 8083MorpholineHCID 10340Sodium Carbonate

Product 1

HCID 958344-(3-Chloropropyl)morpholineYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 1-chloro-3-bromopropane in dry tetrahydrofuran (2 mL) was added to a cold suspension of morpholine (200 mg, 2.29 mmol) and sodium carbonate (0.63 g, 4.56 mmol) in dry tetrahydrofuran (8 mL) at 0° C. The mixture was stirred at 45° C. overnight. The mixture was allowed to cool to rt, filtered and evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with a mixture of ethyl acetate and n-heptane (70:30), afforded 3-chloro-1-morpholin-4-yl-propane (156 mg, 42%).

Workup

  1. temperatureto cool to rt
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customPurification of the residue by silica gel column chromatography
  5. washeluting with a mixture of ethyl acetate and n-heptane (70:30)

Sources & evidence

ORD record
ord-ff547c9213ec4963a635a989c4522fcc
Source dataset
uspto-grants-2009_01
Patent number
US07476682B2

Reaction notes

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