1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523381, compound

HRID 1978480Notes

Reaction equation

HRID 1978480 reaction equation
[N:1]1[CH:2]=[C:3]2[N:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=13)[S:6][C:5]([C:13]([OH:15])=O)=[CH:4]2.ON1C(=O)CCC1=O.C(N=C=NCCCN(C)C)C.Cl.Cl.[NH2:37][CH2:38][C@H:39]1[CH2:44][CH2:43][C@H:42]([CH2:45][N:46]2[CH2:51][CH2:50][CH:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[CH2:48][CH2:47]2)[CH2:41][CH2:40]1>C(#N)C.C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:52]1([CH:49]2[CH2:48][CH2:47][N:46]([CH2:45][C@H:42]3[CH2:43][CH2:44][C@H:39]([CH2:38][NH:37][C:13]([C:5]4[S:6][C:7]5[N:12]6[C:3](=[CH:2][N:1]=[C:11]6[CH:10]=[CH:9][CH:8]=5)[CH:4]=4)=[O:15])[CH2:40][CH2:41]3)[CH2:51][CH2:50]2)[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 10943925HCID 10943925, compoundHCID 178478700HCID 178478700, compound

Product 1

HCID 178523381HCID 178523381, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 0.41 g (1.88 mM) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid and 0.37 g (3.21 mM) of N-hydroxysuccinimide in acetonitrile (5 ml) was added 0.62 g (3.23 mM) of N-ethyl-N′-3-(N,N-dimethylamino)propylcarbodiimide at room temperature, and the mixture was stirred for 1 hour. To this reaction mixture was added a suspension of 0.70 g (1.95 mM) of 1-(trans-4-aminomethyl-1-cyclohexylmethyl)-4-phenylpiperidine dihydrochloride and 1.0 ml (7.71 mM) of triethylamine in chloroform (10 ml) and the mixture was further stirred for 2 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and a small amount of ethanol and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. After concentration, the crude product obtained was purified by column chromatography (methanol/ethyl acetate 30-50%) and recrystallization from ethyl acetate to provide the title compound as red-purple crystals.

Workup

  1. additionTo this reaction mixture was added
  2. stirringthe mixture was further stirred for 2 hours
  3. distillationThe solvent was then distilled off under reduced pressure
  4. additionthe residue was diluted with water
  5. extractiona small amount of ethanol and extracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over MgSO4
  8. concentrationAfter concentration
  9. customthe crude product obtained
  10. customwas purified by column chromatography (methanol/ethyl acetate 30-50%) and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-213306fb8e9f4878aa4f39416ebca18c
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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