Hydrochloric Acid → HCID 67117406, compound

HRID 1784718Notes

Reaction equation

HRID 1784718 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[N:20]1([C:17]2[CH:16]=[CH:15][C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:19][CH:18]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53628957HCID 53628957, compound

Product 1

HCID 67117406HCID 67117406, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of furnished 4-(4-Pyrrolidin-1-yl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester in ethyl acetate (5 mL) was added 4 N hydrogen chloride in ethyl acetate (10 mL) at room temperature. After stirring for 3 h, solvent was removed in vacuo, and the resulting solid was purified by HPLC. Sodium hydroxide was added to the resulting fractions and the aqueous layer was extracted by dichloromethane. Organic layer was washed with brine, and passed through Cerite. Removal of the solvent under reduced pressure afforded 4-(4-pyrrolidin-1-yl-phenyl)-piperidine (1.01 g, 76%).

Workup

  1. customsolvent was removed in vacuo
  2. customthe resulting solid was purified by HPLC
  3. additionSodium hydroxide was added to the resulting fractions
  4. extractionthe aqueous layer was extracted by dichloromethane
  5. washOrganic layer was washed with brine
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-f3042e115b414872ac51f3148119a39d
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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