Dicyclohexylcarbodiimide → HCID 18915886, compound

HRID 1292613Notes

Reaction equation

HRID 1292613 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH2:6][CH2:7][S:8][CH2:9][C:10]([OH:12])=O)=[O:4].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:38]1([CH2:44][C:45]2[CH:46]=[C:47]([CH:53]=[CH:54][CH:55]=2)[O:48][CH2:49][CH2:50][CH2:51][NH2:52])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>ClCCl>[N:38]1([CH2:44][C:45]2[CH:46]=[C:47]([CH:53]=[CH:54][CH:55]=2)[O:48][CH2:49][CH2:50][CH2:51][NH:52][C:10](=[O:12])[CH2:9][S:8][CH2:7][CH2:6][NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 18915893HCID 18915893, compound

Product 1

HCID 18915886HCID 18915886, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

There was dissolved 2.07 g (0.011 mol) of 2-[2-(methoxycarbonylamino)ethylthio]acetic acid in 50 ml of dichloromethane and added 1.68 g (0.011 mol) of HOBt and 2.27 g (0.011 mol) of DCC under cooling with ice, and the mixture was stirred for 30 minutes under cooling with ice. Thereto was added 2.7 g (0.011 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 3.69 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-c2d1b8c91b9f4abc8a9ee72cb4608387
Source dataset
uspto-grants-1998_05
Patent number
US05756822

Reaction notes

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