1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21088448, compound

HRID 350756Notes

Reaction equation

HRID 350756 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:18][CH2:19][CH3:20])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:4][CH:3]=1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[CH3:42][N:43]1[CH2:48][CH2:47][CH:46]([CH2:49][N:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)[CH2:45][CH2:44]1>O.CN(C)C=O>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:18][CH2:19][CH3:20])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([N:53]2[CH2:52][CH2:51][N:50]([CH2:49][CH:46]3[CH2:47][CH2:48][N:43]([CH3:42])[CH2:44][CH2:45]3)[CH2:55][CH2:54]2)=[O:17])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 27369421-((1-Methyl-4-piperidinyl)methyl)piperazineHCID 21088680HCID 21088680, compound

Product 1

HCID 21088448HCID 21088448, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[4-(4-chlorophenyl)-2-propyl-5-oxazolyl]propionic acid (41.7 mg), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (41 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (46 mg), 4-[(1-methyl-4-piperidinyl)methyl]piperazine (60 mg) and N,N-dimethylformamide (0.5 ml) was stirred overnight at room temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated, introduced into preparative HPLC and purified. To the obtained oil was added ethyl acetate, and the mixture was washed with saturated aqueous sodium hydrogen carbonate. A 4N hydrochloric acid ethyl acetate solution was added to the ethyl acetate layer and the mixture was concentrated to give 1-{3-[4-(4-chlorophenyl)-2-propyl-5-oxazolyl]propanoyl}-4-[(1-methyl-4-piperidinyl)methyl]piperazine dihydrochloride (25.0 mg, yield 32%). Recrystallization from ethanol-isopropyl ether gave colorless prism crystals. melting point: 218° c (dec.).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe ethyl acetate layer was concentrated
  3. additionintroduced into preparative HPLC
  4. custompurified
  5. additionTo the obtained oil was added ethyl acetate
  6. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate
  7. additionA 4N hydrochloric acid ethyl acetate solution was added to the ethyl acetate layer
  8. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-ae6ebdd9ee974e1da7c45bd88a0ebcad
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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