1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 66751357, compound

HRID 534902Notes

Reaction equation

HRID 534902 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].[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][O:33][C:34]2[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].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:38]([C:37]2[CH:36]=[CH:35][C:34]([O:33][CH2:32][CH:29]3[CH2:28][CH2:27][N:26]([C:24]([O:23][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:25])[CH2:31][CH2:30]3)=[CH:42][CH:41]=2)=[O:39])[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 66590087HCID 66590087, compoundHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66751357HCID 66751357, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (1.0 g), 4-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methoxy}benzoic acid obtained in Reference Example 6 (1.41 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (824 mg), 1-hydroxy-1H-benzotriazole monohydrate (659 mg), triethylamine (1.53 mL), and N,N-dimethylformamide (10 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 saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (NH-silica gel, 10:90-0:100 hexane/ethyl acetate) to provide the title compound (1.6 g, 87%) as crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography (NH-silica gel, 10:90-0:100 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d5f390196557452190b015d99e3ab84f
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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