Dimethylformamide → 1-[(4-Chlorophenyl)methyl]piperidin-4-one

HRID 456393Notes

Reaction equation

HRID 456393 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[Cl:8][C:9]1[CH:16]=[CH:15]C(CCl)=[CH:11][CH:10]=1.CN([CH:20]=[O:21])C>>[Cl:8][C:9]1[CH:16]=[CH:15][C:2]([CH2:1][N:3]2[CH2:6][CH2:7][C:20](=[O:21])[CH2:5][CH2:4]2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8471Triethylamine

Product 1

HCID 105610671-[(4-Chlorophenyl)methyl]piperidin-4-one

Procedure

To a solution of 4-piperidine trifluoroacetate obtained from step (iv) (853 mg, 4.0 mmol) in DMF was added triethylamine (2.66 mL, 19.2 mmol), followed by 4-chlorobenzyl chloride (753 mg, 4.8 mmol) and the reaction mixture was stirred overnight at room temperature. The volatiles were removed in vacuo, residue was dissolved in ethylacetate, washed with water (H2O), organic layer was dried over sodium sulphate (Na2SO4), filtered and concentrated. The residue was purified by silica gel flash chromatography to give the subtitled compound (350 mg).

Workup

  1. customThe volatiles were removed in vacuo, residue
  2. dissolutionwas dissolved in ethylacetate
  3. washwashed with water (H2O), organic layer
  4. dry with materialwas dried over sodium sulphate (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c01aed61e13749cf93cc2d4a7e8b5f3b
Source dataset
uspto-grants-2007_03
Patent number
US07186718B2

Reaction notes

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