Hydrochloric Acid → 4-Phenylpiperidine-4-carboxamide monohydrochloride

HRID 1682965Notes

Reaction equation

HRID 1682965 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:23].O1CCOCC1>>[ClH:23].[C:17]1([C:11]2([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 227418011-Piperidinecarboxylic acid, 4-(aminocarbonyl)-4-phenyl-, 1,1-dimethylethyl ester

Product 1

HCID 30171294-Phenylpiperidine-4-carboxamide monohydrochloride

Procedure

1-tert-Butoxycarbonyl-4-phenyl-piperidine-4-carboxylic acid amide (0.95 g, 3.12 mmol) was combined with HCl in dioxane (10 mL, 4N, 40 mmol, 13 eq.) at ambient temperature for 1 h. The solvent was concentrated in vacuo and ethyl acetate was added. The slurry was filtered and dried under high vacuum for 48 h to give the title compound: HPLC analysis Rt =5.56 min. using a C-18 column eluting with a acetonitrile:water (0.1% TFA), flow rate=1.0 mL/min., gradient (elution with CH3CN/H2O(0.1%TFA) 10% CH3CN for 10 minutes, 30% CH3CN for 15 minutes, 40% CH3CN for 15 minutes, 50% CH3CN for 10 minutes, and then 100% CH3CN). Analysis: calculated for Cl2H17C1N2O C 59.87; H 7.12; N 11.64; Found C 59.82; H 7.00; N 11.52.

Workup

  1. concentrationThe solvent was concentrated in vacuo and ethyl acetate
  2. additionwas added
  3. filtrationThe slurry was filtered
  4. customdried under high vacuum for 48 h

Sources & evidence

ORD record
ord-16ca58d6ec1a443cae472338e13874a9
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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