Hydrochloric Acid → HCID 20031323, compound

HRID 232264Notes

Reaction equation

HRID 232264 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](Cl)=[O:24])=[CH:18][CH:17]=1.Cl>C(Cl)Cl>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]2)=[O:24])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 906924-Chlorophenylacetyl chlorideHCID 4207714-Piperidinemethanol

Product 1

HCID 20031323HCID 20031323, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.76 g (0.05 mol) of 4-piperidinemethanol and 4.75 g (0.06 mol) of pyridine in 50 mL of methylene chloride cooled to 0° add dropwise a solution of 10.4 g (0.055 mol) of 4-chlorobenzeneacetyl chloride in 25 mL of methylene chloride. When the addition is complete stir the reaction overnight at room temperature. After this time add 25 mL of 2N hydrochloric acid. Separate the layers and wash the methylene chloride layer with two 50 mL portions of saturated sodium bicarbonate solution and 25 mL of saturated sodium chloride solution then dry the methylene chloride layer over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo to obtain the title compound.

Workup

  1. additionWhen the addition
  2. customthe reaction overnight at room temperature
  3. customSeparate the layers
  4. washwash the methylene chloride layer with two 50 mL portions of saturated sodium bicarbonate solution and 25 mL of saturated sodium chloride solution
  5. dry with materialthen dry the methylene chloride layer over anhydrous sodium sulfate
  6. filtrationFilter the drying agent
  7. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-6ab4cdbdcb4f43368096b6d3f5df236d
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Reaction notes

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