Diisopropylamine → HCID 69519748, compound

HRID 1831369Notes

Reaction equation

HRID 1831369 reaction equation
Cl.Cl.[CH:3]1([N:9]([CH3:16])[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][N:29]=2)=[CH:23][CH:22]=1)=[O:19].C(NC(C)C)(C)C>CN(C)C=O.O1CCCC1>[F:36][C:34]([F:35])([F:37])[C:31]1[CH:32]=[CH:33][C:28]([O:27][C:24]2[CH:25]=[CH:26][C:21]([O:20][C:18]([N:13]3[CH2:12][CH2:11][CH:10]([N:9]([CH:3]4[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]4)[CH3:16])[CH2:15][CH2:14]3)=[O:19])=[CH:22][CH:23]=2)=[N:29][CH:30]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 220477624-(5-Trifluoromethylpyridin-2-yloxy)-phenyl chloroformateHCID 56831596HCID 56831596, compound

Product 1

HCID 69519748HCID 69519748, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

The title product was prepared from cyclohexyl-methyl-piperidin-4-yl-amine, dihydrochloride and 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl chloroformate, 2 equivalent of diisopropylamine; dimethylformamide/tetrahydrofuran (2:1). The reaction mixture was evaporated to dryness and the crude product extracted with ethyl acetate from an aqueous HCl solution saturated with sodium chloride, pH 1–2. The title product was crystallized from ethyl acetate during evaporation of the solvent, filtered and dryed in vacoum (45%, white crystals). HPLC-MS m/z=478.2 (M+1), Rt: 3.10 min.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. extractionthe crude product extracted with ethyl acetate from an aqueous HCl solution saturated with sodium chloride, pH 1–2
  3. customThe title product was crystallized from ethyl acetate during evaporation of the solvent
  4. filtrationfiltered

Sources & evidence

ORD record
ord-07aecb79ae77417baa48070a4b83cf73
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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