Piperidine-1-propylamine → HCID 44603110, compound

HRID 1685395Notes

Reaction equation

HRID 1685395 reaction equation
[CH2:1]([N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([OH:20])=O)[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[N:43]1([CH2:49][CH2:50][CH2:51][NH2:52])[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1>ClCCl.CC(=O)OCC.CO>[CH2:1]([N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([NH:52][CH2:51][CH2:50][CH2:49][N:43]3[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]3)=[O:20])[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 19049Piperidine-1-propylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67265769HCID 67265769, compound2×

Product 1

HCID 44603110HCID 44603110, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen atmosphere, 2-benzyl-3-oxoisoindoline-5-carboxylic acid (Chemical Formula 8) (100 mg, 0.374 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 0.144 g, 0.749 mmol), and 1-hydroxybenzotriazole (HOBT, 0.025 g, 0.187 mmol) were reacted at room temperature in distilled dichloromethane, with stirring, for 2 hours. After monitoring through TLC [CH2Cl2:MeOH=4:1], the temperature was decreased to −40° C. at which time 3-(piperidin-1-yl)propan-1-amine (80 μL, 0.562 mmol) was added before stirring for 3-4 hours. The reaction progress was monitored with TLC [Hex: EA=1:1]. When the reaction was completed, the reaction mixture was extracted with NaHCO3 and then with CH2Cl2. The organic layer thus obtained was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in a vacuum and the concentrate was purified using column chromatography [CH2Cl2:MeOH=20:1] to afford 2-benzyl-3-oxo-N-(3-(piperidin-1-yl)propyl)isoindoline-5-carboxamide (Chemical Formula 1) in an amount of 96 mg (Yield 73%). This product was solidified with ethereal HCl to give a hydrochloride.

Workup

  1. additionwas added
  2. stirringbefore stirring for 3-4 hours
  3. extractionthe reaction mixture was extracted with NaHCO3
  4. customThe organic layer thus obtained
  5. dry with materialwas dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in a vacuum
  8. customthe concentrate was purified

Sources & evidence

ORD record
ord-7c61a7af2b9046328b365c4207562337
Source dataset
uspto-grants-2012_04
Patent number
US08148402B2

Reaction notes

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