Hydrogen chloride-ethyl acetate → 3-[2-(4-Piperidinyl)ethyl]benzamide hydrochloride

HRID 2074301Notes

Reaction equation

HRID 2074301 reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[CH:7]=[CH:8][CH:9]=1)=[O:3].[ClH:25].CCOC(C)=O>CCOC(C)=O>[ClH:25].[NH:15]1[CH2:16][CH2:17][CH:12]([CH2:11][CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:2]([NH2:1])=[O:3])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57421827Tert-butyl 4-{2-[3-(aminocarbonyl)phenyl]ethyl}-1-piperidinecarboxylate

Product 1

HCID 574218283-[2-(4-Piperidinyl)ethyl]benzamide hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl 4-{2-[3-(aminocarbonyl)phenyl]ethyl}-1-piperidinecarboxylate (13.8 g) was dissolved in EtOAc (200 ml), and 4 M hydrogen chloride/EtOAc solution (130 ml) was added thereto, followed by stirring at room temperature for 4 hours, and then concentrated. Acetonitrile was added to the resulting residue, followed by heating, and the precipitated crystal was collected by filtration, washed with EtOAc, and dried under reduced pressure to obtain 3-[2-(4-piperidinyl)ethyl]benzamide hydrochloride (11.2 g).

Workup

  1. concentrationconcentrated
  2. additionAcetonitrile was added to the resulting residue
  3. temperatureby heating
  4. filtrationthe precipitated crystal was collected by filtration
  5. washwashed with EtOAc
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-091cfa9bf08444d2ac4376949ad984ef
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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