Water → HCID 66975431, compound

HRID 1022598Notes

Reaction equation

HRID 1022598 reaction equation
[CH2:1]([NH:8][CH2:9][CH:10]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH:11]1[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:33][CH2:34][C:35](Cl)=[O:36].O>C1COCC1>[CH2:1]([N:8]([CH2:9][CH:10]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH:11]1[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12]1)[C:35](=[O:36])[CH2:34][Cl:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66975653HCID 66975653, compound

Product 1

HCID 66975431HCID 66975431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS)—N-benzyl-2-(3,4-dichlorophenyl)-2-[(4SR)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanamine (3.72 g) and triethylamine (1.63 ml) in THF (30 ml) was added chloroacetyl chloride (0.783 ml) at 0° C., and the reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.99 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8907b670e36c419983f3f20d323d20ce
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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