Potassium Carbonate → 4-[4-(4-Chlorophenyl)-4-hydroxy-piperidin-1-yl]1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}1,3,5-triazin-2(1H)-one

HRID 1477616Notes

Reaction equation

HRID 1477616 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:21])[CH2:13][CH2:12][N:11]([C:14]3[N:19]=[CH:18][NH:17][C:16](=[O:20])[N:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.OC1(C2C=CC=CC=2)CCN(C2N=CNC(=O)N=2)CC1.CC1C=CC(S(O[CH2:53][C:54]2[S:55][C:56]([C:59]([F:62])([F:61])[F:60])=[CH:57][CH:58]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:21])[CH2:13][CH2:12][N:11]([C:14]3[N:19]=[CH:18][N:17]([CH2:53][C:54]4[S:55][C:56]([C:59]([F:62])([F:61])[F:60])=[CH:57][CH:58]=4)[C:16](=[O:20])[N:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 117839221[5-(Trifluoromethyl)thiophen-2-yl]methyl 4-methylbenzenesulfonateHCID 178517888HCID 178517888, compoundHCID 178517889HCID 178517889, compound

Product 1

HCID 1178393994-[4-(4-Chlorophenyl)-4-hydroxy-piperidin-1-yl]1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}1,3,5-triazin-2(1H)-one

Procedure

A mixture (100 mg) of 4-[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]-1,3,5-triazin-2(1H)-one synthesized in Reference Synthesis Example 22a and 4-(4-hydroxy-4-phenylpiperidin-1-yl)-1,3,5-triazin-2(1H)-one, [5-(trifluoromethyl)thiophen-2-yl]methyl 4-methylbenzenesulfonate (558 mg, 0.65 mmol) synthesized in Reference Synthesis Example 51, and potassium carbonate (180 mg, 1.30 mmol) were used to obtain a mixture of compounds in Reference Synthesis Examples 92a and 92b being the title compounds (21 mg) by synthesis in a similar manner to Reference Synthesis Example 91.

Workup

  1. customto obtain
  2. additiona mixture of compounds
  3. customby synthesis in a similar manner
  4. customto Reference Synthesis Example 91

Sources & evidence

ORD record
ord-52c95ccdc61848858fdacbf2f1caa666
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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