4-Chlorobutyryl chloride → HCID 67427949, compound

HRID 1181521Notes

Reaction equation

HRID 1181521 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[CH2:8]([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][CH:22]([CH3:24])[CH3:23])[CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCN(C(C)C)C(C)C>ClCCl>[CH2:8]([N:15]1[CH2:20][CH2:19][CH:18]([N:21]([CH:22]([CH3:24])[CH3:23])[C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])[CH2:17][CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 81531DiisopropylethylamineHCID 107283101-Benzyl-N-isopropylpiperidin-4-amine

Product 1

HCID 67427949HCID 67427949, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-chlorobutyryl chloride (5.3 m]L, 47.4 mmol) in dichloromethane (400 mL) was added dropwise to a mixture of 1-benzyl-4-(isopropylamino)piperidine (10 g, 43.07 mmol) and DIPEA (9.0 mL, 51.7 mmol) in dichloromethane (200 mL) at 0° C. The reaction mixture was stirred at 0° C. for 15 min and then at room temperature for 2 h. The solution was then washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (ethyl acetate/hexane/triethylamine: 42.5/56.5/1) to give 5.0 g of the title intermediate as viscous oil (35% yield).

Workup

  1. waitat room temperature for 2 h
  2. washThe solution was then washed with saturated sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (ethyl acetate/hexane/triethylamine: 42.5/56.5/1)

Sources & evidence

ORD record
ord-048da5d1db6e4d038973212d9dd9cfdb
Source dataset
uspto-grants-2007_10
Patent number
US07285564B2

Reaction notes

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