Water → Hydrochloric Acid

HRID 437239Notes

Reaction equation

HRID 437239 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=[O:6].[C:14]([NH:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>Cl.CCOCC>[C:14]([NH:22][CH:23]1[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[O:6])[CH2:25][CH2:24]1)(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1.[ClH:1]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 118120N-4-PiperidylbenzamideHCID 27237814,4'-Dichlorobutyrophenone

Product 2

HCID 313Hydrochloric AcidYield 521.8%HCID 102713911-[3-(4-Chlorobenzoyl)propyl]-4-benzamidopiperidine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

4-Chloro-4'-chlorobutyrophenone (2.17 g.) was added to a well-ground mixtue of 4-benzamidopiperidine (2.04 g.) and anhydrous potassium carbonate (1.38 g.) and the mixture heated to 100° C. for 1 hour. The solid residue was slurried with hot water (100 ml.) for 3 hours, filtered, washed with ether and dried to give a cream coloured solid. This solid was dissolved in ethanolic hydrogen chloride, treated with ether and then cooled to 0° C. to give the title compound as its hydrochloride (1.9 g.) m.p. 242°-243° C. (Found: C, 62.8; H, 6.2; N, 6.55. C22H25ClN2O2. HCl requires C, 62.7; H, 6.0; N, 6.65%).

Workup

  1. filtrationfiltered
  2. washwashed with ether
  3. customdried
  4. customto give a cream
  5. temperaturecooled to 0° C.

Sources & evidence

ORD record
ord-414e4fe57a6e4947984d95080e07bc18
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Reaction notes

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