1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 19379068, compound

HRID 2210545Notes

Reaction equation

HRID 2210545 reaction equation
[C:1]([OH:11])(=O)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.[CH:33]1([O:38][C:39]2[CH:40]=[C:41]([CH:47]3[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]3)[CH:42]=[CH:43][C:44]=2[O:45][CH3:46])[CH2:37][CH2:36][CH2:35][CH2:34]1>C(Cl)Cl>[CH:33]1([O:38][C:39]2[CH:40]=[C:41]([CH:47]3[CH2:48][CH2:49][N:50]([C:1](=[O:11])/[CH:2]=[CH:3]/[C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH2:51][CH2:52]3)[CH:42]=[CH:43][C:44]=2[O:45][CH3:46])[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 444539Cinnamic AcidHCID 15295460HCID 15295460, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 19379068HCID 19379068, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of trans-cinnamic acid (1.20 mmol, 0.178 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (DEC; 1.20 mmol, 0.230 g) and hydroxybenzotriazole (HOBT; 1.20 mmol, 0.162 g) was dissolved in dry CH2Cl2 (20 mL) and stirred at room temperature for 1.5 hours. To this solution was added 4-(3-cyclopentyloxy-4-methoxyphenyl)piperidine (1.00 mmol, 0.275 g) in dry CH2Cl2 (10 mL) dropwise over 10 minutes and the resulting solution was stirred at room temperature overnight. The volatiles were removed in vacuo and the residue was partitioned between EtOAc (70 mL) and 1N NaOH (70 mL). The aqueous phase was extracted with EtOAc (1×70 mL), the combined organics washed with H2O (1×70 mL), dried (Na2SO4) and concentrated in vacuo to yield a colorless oil. Purification by flash chromatography (SiO2 : 5% EtOAc/CH2Cl2) afforded the title compound as a white solid, mp=93°-95° C. (0.385 g, 95%).

Workup

  1. stirringthe resulting solution was stirred at room temperature overnight
  2. customThe volatiles were removed in vacuo
  3. customthe residue was partitioned between EtOAc (70 mL) and 1N NaOH (70 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (1×70 mL)
  5. washthe combined organics washed with H2O (1×70 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto yield a colorless oil
  9. customPurification by flash chromatography (SiO2 : 5% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-088412db09e046c1bc37e3992694e675
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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