1-Bromo-3-chloropropane → HCID 69418516, compound

HRID 1375034Notes

Reaction equation

HRID 1375034 reaction equation
Cl.[CH3:2][O:3][CH2:4][C@H:5]1[O:10][CH2:9][CH2:8][NH:7][CH2:6]1.Br[CH2:12][CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[ClH:15].[Cl:15][CH2:14][CH2:13][CH2:12][N:7]1[CH2:8][CH2:9][O:10][C@H:5]([CH2:4][O:3][CH3:2])[CH2:6]1

Participants

7

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 53338717(2S)-2-(Methoxymethyl)morpholine--hydrogen chloride (1/1)

Product 1

HCID 69418516HCID 69418516, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S)-2-(methoxymethyl)morpholine hydrochloride (0.5 g), 1-bromo-3-chloropropane (1.47 ml) and potassium carbonate (2.06 g) in N,N-dimethylformamide (6 ml) was stirred at room temperature for 1 hour. After ethyl acetate and water were added to the mixture, the organic layer was separated, washed with water twice, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate as an eluent. The fractions containing the objective compound were collected and evaporated under reduced pressure. The resulting oil was treated with 4N hydrogen chloride in ethyl acetate to give (2S)-4-(3-chloropropyl)-2-(methoxymethyl)morpholine hydrochloride (0.44 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with water twice
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. additionThe fractions containing the objective compound
  7. customwere collected
  8. customevaporated under reduced pressure
  9. additionThe resulting oil was treated with 4N hydrogen chloride in ethyl acetate

Sources & evidence

ORD record
ord-7757821035044b2699d788c96731d326
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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