Chloroacetyl chloride → HCID 86718433, compound

HRID 1523402Notes

Reaction equation

HRID 1523402 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[CH:4][C:3]=1[F:22].C(N(CC)CC)C.[Cl:30][CH2:31][C:32](Cl)=[O:33]>ClCCl>[Cl:30][CH2:31][C:32]([NH:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[CH2:11][CH2:12]2)=[CH:4][C:3]=1[F:22])=[O:33]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 86718432HCID 86718432, compound

Product 1

HCID 86718433HCID 86718433, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 4-(4-amino-3-fluoro phenoxy)piperidine-1-carboxylate (7.54 g, 0.024 moles) was dissolved in dichloromethane (100 mL) and added triethylamine (3.6 g, 0.036 moles) at room temperature. To the resulting mass, a solution of chloro acetyl chloride (2.9 g, 0.026 moles) in dichloromethane (15 mL) was added drop wise at room temperature. After completion of the reaction, the organic mass was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to obtain the crude residue, which was further purified by flash chromatography using (ethyl acetate:hexane, 1:5) to afford the title compound 5.94 g (Yield: 64%).

Workup

  1. customAfter completion of the reaction
  2. washthe organic mass was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain the crude residue, which
  6. customwas further purified by flash chromatography

Sources & evidence

ORD record
ord-a02af14f541e47e68a344478b8e761e2
Source dataset
uspto-grants-2015_07
Patent number
US09079888B2

Reaction notes

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