1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21940073, compound

HRID 1242947Notes

Reaction equation

HRID 1242947 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[O:10])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.CN(C1C=CC=CN=1)C.[CH2:47]([O:54][C:55]([N:57]1[CH2:62][CH2:61][CH:60]([C:63](O)=[O:64])[CH2:59][CH2:58]1)=[O:56])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C(OCC)(=O)C.O.O1CCCC1.C(N(CC)CC)C>[CH3:16][N:14]([CH3:15])[CH2:13][CH2:12][NH:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:63]([CH:60]2[CH2:61][CH2:62][N:57]([C:55]([O:54][CH2:47][C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)=[O:56])[CH2:58][CH2:59]2)=[O:64])=[CH:7][CH:6]=1

Participants

10

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidHCID 10704226HCID 10704226, compound

Product 1

HCID 21940073HCID 21940073, compoundYield 49.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Aminophenyl)-N-[2-(dimethylamino)ethyl]acetamide (221 mg), WSC (249 mg), 1-hydroxybenzotriazole (199 mg), triethylamine (0.4 ml), and dimethylaminopyridine (244 mg) were added to a tetrahydrofuran (10 ml) solution of 1-[(benzyloxy)carbonyl]-4-piperidinecarboxylic acid (290 mg), which was stirred for 20 hours. The reaction mixture was poured into water, and extraction was conducted using ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, dried over sodium sulfate, and then concentrated. The residue was recrystallized from methanol-diisopropyl ether, to give the titled compound (230 mg).

Workup

  1. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was recrystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-ed362a553ed245edb6640e08ef722fc7
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

Loading…