1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}piperidin-2-one

HRID 534879Notes

Reaction equation

HRID 534879 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[O:19]=[C:20]1[NH:25][CH:24]([C:26](O)=[O:27])[CH2:23][CH2:22][CH2:21]1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>O.CN(C)C=O.C(N(CC)CC)C>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:26]([CH:24]2[NH:25][C:20](=[O:19])[CH2:21][CH2:22][CH2:23]2)=[O:27])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 30142376-Oxo-piperidine-2-carboxylic acidHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 667927166-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}piperidin-2-oneYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (500 mg), 6-oxopiperidine-2-carboxylic acid (261 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (403 mg), 1-hydroxy-1H-benzotriazole monohydrate (322 mg), triethylamine (0.627 mL), and N,N-dimethylformamide (5 mL) was stirred at room temperature for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with 1 M sodium hydroxide solution, saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (280 mg, 47%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with 1 M sodium hydroxide solution, saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c4ec19c90f85459a88f5a4f490838434
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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