1,2-Dichloroethane → HCID 18665729, compound

HRID 365457Notes

Reaction equation

HRID 365457 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([OH:18])[CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15](O)=[O:16])[CH2:10]1.[CH2:25](Cl)CCl.[CH:29]1[CH:30]=[CH:31][C:32]2N(O)N=N[C:33]=2[CH:34]=1.[CH3:39][N:40]1CCOCC1.Cl.Cl.C(C1C=CC(C[C:55]2([N:62]=[CH:61][N:60]=[CH:59]2)[CH2:56][CH2:57][NH2:58])=CC=1)#N>CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([OH:18])[CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15](=[O:16])[NH:58][CH2:57][CH2:56][C:55]2[N:62]([CH2:25][C:29]3[CH:30]=[CH:31][C:32]([C:39]#[N:40])=[CH:33][CH:34]=3)[CH:61]=[N:60][CH:59]=2)[CH2:10]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 18665742HCID 18665742, compoundHCID 70272451HCID 70272451, compound

Product 1

HCID 18665729HCID 18665729, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[2-(2-Pyridyl)-2-phenyl-2-hydroxyethyl]piperidine-3(S)-carboxylic acid (0.172 g, 0.527 mmol) was suspended in DMF (5 mL) and treated with EDC (0.106 g, 0.553 mmol), HOBT (0.068 g, 0.501 mmol), followed by N-methylmorpholine to adjust the pH to 7, and 4-(4-Cyanobenzyl) histamine dihydrochloride (0.158 g, 0.527 mmol). stirring at ambient temperature for 18 hr under N2, the reaction mixture was concentrated, partitioned between CH2Cl2 and H2O, the organic phase washed with aq satd NaHCO3 soln, brine, and dried (Na2SO4). Filtration and concentration to dryness gave the title compound after purification by RP HPLC on a Waters Prep Pak eluting with 0.1%TFA/H2O: 0.1%TFA/CH3CN, 95:5 to 5:95. FAB MS (M+1) 535.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompartitioned between CH2Cl2 and H2O
  3. washthe organic phase washed with aq satd NaHCO3 soln
  4. dry with materialbrine, and dried (Na2SO4)
  5. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-0e2aba1138a5486bacc95334f433d50e
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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