Hydrochloric Acid → 148583-64-6

HRID 1721601Notes

Reaction equation

HRID 1721601 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](Cl)=[O:13].Cl>O1CCCC1>[Cl:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 27333243-(Chloromethyl)benzoyl chloride

Product 1

HCID 10014405148583-64-6Yield 86,436.797%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of piperidine (67.6 g, 0.793 mole) in tetrahydrofuran (1 L) was added dropwise a solution of 3-chloromethylbenzoyl chloride (100.0 g, 0.529 mmol). When the addition was complete, the reaction mixture was allowed to warm to ambient temperature and was left to stir overnight. The reaction mixture was poured into a solution of 1N hydrochloric acid. This solution was extracted with diethyl ether. The ether extracts were combined, washed with water, dried (MgSO4), and concentrated to afford 108.7 g (86%) of N-(3-(chloromethyl)benzoyl)piperidine (10) as a pale yellow oil whose 1H NMR in CDCl3 supported the structure.

Workup

  1. additionWhen the addition
  2. waitwas left
  3. extractionThis solution was extracted with diethyl ether
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-109c7b41765d40ada47037098d6823a0
Source dataset
uspto-grants-1996_04
Patent number
US05512566

Reaction notes

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