Potassium Carbonate → N-piperidin-4-yl-4-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-butyramide

HRID 511124Notes

Reaction equation

HRID 511124 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:35])[CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(OC(=O)C)C>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:35])[CH2:16][CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][N:22]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:29][CH:30]=3)[CH2:23][CH2:24]2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 585766414-{4-[4-(4-Trifluoromethyl-phenyl)-piperazin-1-yl]-butyrylamino}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58576583N-piperidin-4-yl-4-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-butyramideYield 79.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluororoacetic acid (1 mL) is added to a solution of 4-{4-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-butyrylamino}-piperidine-1-carboxylic acid tert-butyl ester (660 mg; 1.32 mmol, prepared in accordance with Example 74) in dichloromethane (4 mL) and the resulting mixture is stirred at room temperature. After 3 hours reaction time, the excess acid is neutralized by the addition of potassium carbonate, the mixture is filtered and the filtrate is concentrated under reduced pressure. The residue obtained is diluted in ethylacetate (20 mL) and the organic phase is extracted with water (2×10 mL). The combined aqueous phases are extracted with dichloromethane (10 mL) and diethylether (10 mL). The combined organic layers are dried over magnesium sulfate and the solvents removed under reduced pressure to afford the desired product (417 mg; 1.05 mmol).

Workup

  1. customAfter 3 hours reaction time
  2. filtrationthe mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue obtained
  5. extractionthe organic phase is extracted with water (2×10 mL)
  6. extractionThe combined aqueous phases are extracted with dichloromethane (10 mL) and diethylether (10 mL)
  7. dry with materialThe combined organic layers are dried over magnesium sulfate
  8. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-b6bc6b82201346ba9113bb924051fee5
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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