Dicyclohexylcarbodiimide → HCID 18915895, compound

HRID 1379618Notes

Reaction equation

HRID 1379618 reaction equation
[CH2:1]([O:3][C:4]([NH:6][CH2:7][CH2:8][S:9][CH2:10][C:11]([OH:13])=O)=[O:5])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:39]1([CH2:45][C:46]2[CH:47]=[C:48]([CH:54]=[CH:55][CH:56]=2)[O:49][CH2:50][CH2:51][CH2:52][NH2:53])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>ClCCl>[N:39]1([CH2:45][C:46]2[CH:47]=[C:48]([CH:54]=[CH:55][CH:56]=2)[O:49][CH2:50][CH2:51][CH2:52][NH:53][C:11](=[O:13])[CH2:10][S:9][CH2:8][CH2:7][NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 18915881HCID 18915881, compound

Product 1

HCID 18915895HCID 18915895, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

There was dissolved 2.5 g (0.012 mol) of 2-[2-(ethoxycarbonylamino)ethylthio]acetic acid in 60 ml of dichloromethane and added 1.85 g (0.012 mol) of HOBt and 2.5 g (0.012 mol) of DCC under cooling with ice, and the mixture was stirred for 30 minutes under cooling with ice. Thereto was added 3.0 g (0.012 mol) of 3-[3-(piperidinomethyl)phenoxy]propylamine and the mixture was stirred for 18 hours at room temperature. The precipitate was filtrated off, and the filtrate was washed with 5% aqueous solution of sodium hydroxide and with water and dried over Glauber's salt. Then the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=5:1) to give 4.23 g of the titled compound as oily matter.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred for 18 hours at room temperature
  4. filtrationThe precipitate was filtrated off
  5. washthe filtrate was washed with 5% aqueous solution of sodium hydroxide and with water
  6. dry with materialdried over Glauber's salt
  7. customThen the solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-10a90dd991b342e1ae460880c148768c
Source dataset
uspto-grants-1997_09
Patent number
US05672597

Reaction notes

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