1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68592716, compound

HRID 2190541Notes

Reaction equation

HRID 2190541 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[CH2:29][CH2:28][CH2:27]2.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20](=[O:22])[NH:23][C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[CH2:29][CH2:28][CH2:27]4)=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 90496Indan-5-amineHCID 27955084-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acid

Product 1

HCID 68592716HCID 68592716, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(4-carboxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (918 mg, 3 mmol) and 5-aminoindan (399 mg, 3 mmol) in methylene chloride (30 mL) was added EDCI (580 mg, 3 mmol) and DMAP (20 mg, 0.16 mmol). The mixture was stirred at room temperature overnight and then extracted with methylene chloride (50 mL) and aqueous hydrochloric acid (1N, 20 mL). The organic layer was washed with water, then sodium hydroxide solution and finally with water and brine. The solution was dried over sodium sulfate and filtered. Solvents were evaporated and the residue was crystallized from ethyl acetate (40 mL) to give 4-[4-(indan-5-ylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester. This intermediate was dissolved in methylene chloride (5 mL) and trifluoroacetic acid (3 mL). The mixture was stirred at room temperature for 1 hr and solvents were evaporated. The residue was extracted with methylene chloride and 1N sodium hydroxide solution. The organic layer was washed with brine and dried over sodium sulfate. The product, N-indan-5-yl-4-piperazin-1-yl-benzamide was obtained after solvent evaporation (450 mg, Yield: 47%). LCMS calc for C20H23N3O (m/e) 321.42, obsd 322.5 (M+H).

Workup

  1. extractionextracted with methylene chloride (50 mL) and aqueous hydrochloric acid (1N, 20 mL)
  2. washThe organic layer was washed with water
  3. dry with materialThe solution was dried over sodium sulfate
  4. filtrationfiltered
  5. customSolvents were evaporated
  6. customthe residue was crystallized from ethyl acetate (40 mL)

Sources & evidence

ORD record
ord-c7295a78f7cf4ac7ba7ea3a82ee0019d
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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