2,4-Dichlorobenzyl chloride → HCID 11624258, compound

HRID 2235293Notes

Reaction equation

HRID 2235293 reaction equation
[Li+].CC([N-]C(C)C)C.[CH:9]1([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]2=[O:21])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[CH2:30]Cl>C1COCC1.C(OCC)(=O)C>[Cl:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[CH2:30][CH:17]1[CH2:18][CH2:19][CH2:20][N:15]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[C:16]1=[O:21]

Participants

6

Reactant 3

HCID 72122,4-Dichlorobenzyl chlorideHCID 2724682Lithium diisopropylamideHCID 14178413HCID 14178413, compound

Product 1

HCID 11624258HCID 11624258, compoundYield 242%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 1.8 M LDA (0.9 mL, 1.7 mmol) to solution of 1-cyclohexylpiperidin-2-one (300 mg, 1.7 mmol) in THF (5 mL) at −78° C. and stir for 15 minutes. Add 2,4-dichloro-1-(chloromethyl)benzene (640 mg, 3.3 mmol) and warm the reaction to room temperature. Quench the reaction with water and dilute with ethyl acetate. Dry the organic layer with sodium sulfate, filter and concentrate. Purify the residue by biotage chromatography to afford the title compound as a white solid (1.4 g, 81%): MS (APCI-pos mode) m/z (rel intensity): 340.2 (M+H).

Workup

  1. customthe reaction to room temperature
  2. customQuench
  3. customthe reaction with water
  4. dry with materialDry the organic layer with sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue by biotage chromatography

Sources & evidence

ORD record
ord-2f521877916c4f98ae061b0d2a0c2035
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

Loading…