1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66805508, compound
Reaction equation
[N:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:42][N:43]([CH:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)[C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47]>ClCCl.C(OCC)(=O)C>[CH3:42][N:43]([CH:51]1[CH2:52][CH2:53][N:54]([C:9](=[O:11])[CH2:8][CH2:7][N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:55][CH2:56]1)[C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:47])[CH3:48]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
3-(Piperidin-1-yl)propanoic acid (3.183 mmol, 1.0 eq) was dissolved in dichloromethane (40 ml) and DIPEA (7.958 mmol, 2.5 eq) and cooled to 0° C.; EDCI (3.82 mmol, 1.2 eq) and HOBT (0.637 mmol, 0.2 eq) were added and stirring was carried out for 15 hours at RT. The mixture was then cooled to 0° C. again, tert-butyl methyl(piperidin-4-yl)carbamate (3.183 mmol, 1.0 eq) was added, and the reaction mixture was stirred for 16 hours at RT. Then the reaction mixture was diluted with ethyl acetate, washed with 10% ammonium chloride solution, sat. NaHCO3 solution and with sat. NaCl solution, dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography (silica gel, ethyl acetate/ethanol). Yield: 78%
Workup
- stirringthe reaction mixture was stirred for 16 hours at RT
- washwashed with 10% ammonium chloride solution, sat. NaHCO3 solution and with sat. NaCl solution
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe crude product was purified by column chromatography (silica gel, ethyl acetate/ethanol)
Sources & evidence
- ORD record
- ord-bfa58c16f140411e9d005164a8aef5da
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680159B2
Reaction notes
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