Heptane → HCID 15515186, compound

HRID 1683857Notes

Reaction equation

HRID 1683857 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14]Br)=[CH:10][CH:9]=2)[CH:4]=[N:3]1.[F:16][C:17]([F:45])([F:44])[O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([C:33]2[CH:38]=[CH:37][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:35][CH:34]=2)([OH:32])[CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:21][CH:20]=1.C(N(CC)C(C)C)(C)C.CCCCCCC>CS(C)=O.C(OCC)(=O)C>[CH3:1][N:2]1[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:29]3[CH2:30][CH2:31][CH:26]([C:25]([C:22]4[CH:21]=[CH:20][C:19]([O:18][C:17]([F:16])([F:44])[F:45])=[CH:24][CH:23]=4)([C:33]4[CH:38]=[CH:37][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:35][CH:34]=4)[OH:32])[CH2:27][CH2:28]3)=[CH:10][CH:9]=2)[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 8900HeptaneHCID 81531DiisopropylethylamineHCID 190409264-[Bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidineHCID 22006937HCID 22006937, compound

Product 1

HCID 15515186HCID 15515186, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

This compound was prepared in a manner analogous to that of Step D of Example 12, with 2.0 grams (0.007 mole) of 4,5-dihydro-1-methyl-5-oxo-4-(4-bromomethylphenyl)-1H-1,2,4-triazole, 2.0 grams (0.005 mole) of 4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine (prepared as in Step C of Example 12), and 3.2 grams (0.025 mole) of N,N-diisopropylethylamine in about 15 mL of dimethyl sulfoxide as reagents. The crude reaction product was subjected to column chromatography on silica gel, with 2:8 heptane:ethyl acetate, and then pure ethyl acetate as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding 1.6 grams of N-[4-(4,5-dihydro-1-methyl-5-oxo-1H-1,2,4-triazol-4-yl)phenylmethyl]-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step D of Example 12
  2. customThe crude reaction product
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ddedc8cd7d94868b217535c86cbd85c
Source dataset
uspto-grants-1997_06
Patent number
US05639763

Reaction notes

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